


Sixteen Years In Hell

by gaydestiny



Category: Teen Wolf (TV)
Genre: Alternate Universe - Human, Blow Jobs, First Time, Humor, Hurt/Comfort, Intercrural Sex, M/M, Non-Graphic Violence, POV Stiles, Prison, Rimming, Sexual Content, Unresolved Sexual Tension
Language: English
Status: Completed
Published: 2012-08-22
Updated: 2014-04-06
Packaged: 2017-11-12 17:52:14
Rating: Explicit
Warnings: Underage
Chapters: 7
Words: 23,914
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/494027
Author URL: https://archiveofourown.org/users/gaydestiny/pseuds/gaydestiny
Summary: <blockquote class="userstuff">
              <p>So this was finally it. He was being escorted by an armed guard through a pair of double doors and into actual prison. Where he would be sharing living quarters with convicted killers, probably. Stiles may have been a bit of a badass in his own right, but he was still just a 16 year old kid, he used to be an honor student for fuck's sake, how was he supposed to deal with this?</p>
            </blockquote>





	1. Chapter 1

**Author's Note:**

> **Original Notes**  
>  1.) Stiles' dad is not the sheriff  
> 2.) The title is taken from the ACDC song "Jailbreak"  
> 3.) It starts off pretty angsty but the rest of the story is not AT ALL  
> 4.) I have a pretty limited knowledge of the judicial system and in some spots you're probably just gonna have to go with it and give me some artistic liberties
> 
>  **Updated Notes**  
>  This WIP has been haunting me for almost two years, and now that it’s finally done I decided to go through and change some bits and take out the notes on all the chapters so you don’t have to suffer through me apologizing for updating so slowly every time.
> 
> ALSO, since I had a couple of people point this out to me, this is set in a complete alternate universe where people can go to prison at 16 (even though I looked this up and I was pretty sure that you could?? But I guess I was wrong lol whatever).
> 
> I was also picturing the prison to look like the place from Orange Is The New Black except with guys… and regular cell blocks… I’M THE WRITER I CAN DO WHAT I WANT I’M SORRY THE STORY JUST WORKS BETTER LIKE THAT. That’s it I think. I hope you enjoy this fic that tortured me for 19+ months! 
> 
> (Also, this story almost definitely would not have ever been finished if it weren't for the people who left comments and sent me messages on Tumblr asking me to continue writing, so a very sincere thank you to everyone who encouraged me! I love you all)

It starts with a fire. 

Well, it doesn't _exactly_ start there. 

It starts when Stiles is fifteen. Fifteen and reckless and alive with the possibilities of the rest of his life. Fifteen and happy, and smart, and maybe a bit overly snarky and sarcastic, but it doesn't matter because when you're fifteen, nothing matters.

Fifteen, and never even had to deal with so much as a pet goldfish dying. And then his mom gets cancer. The happiness is gone, or at least lost somewhere he isn't able to find it. Lost in a sea of doctor's appointments and chemo and his dad's drinking problem which has reared it's ugly head, and Stiles stops believing that he'll ever feel happy again; ever feel anything besides hopelessness and guilt and pain.

When she dies, he's almost relieved. He probably would've done the deed himself if he'd had to watch her lying there in bed for another day. 

Once she's gone, he doesn't know what to do. So he does nothing. He smokes cigarettes out by the old rock quarry and he steals from whatever stores he feels like, depending on his mood, just to feel a little thrill. He doesn't pay much attention to his dad, because he knows if he bothered to look all he'd find would be a shell of a man slumped over in his armchair with half a bottle of bourbon in one hand and an old polaroid picture of his mom in the other. 

So no, it doesn't start with a fire, but when Stiles is sixteen and no closer to knowing how to deal with his mom's death than he was a year ago, he does something stupid. 

And honestly it wasn't even on purpose, which makes it even worse. Just a cigarette butt carelessly tossed aside onto some dry grass, which just happened to be on the front lawn of the largest abandoned building in town, the old Beacon Hills Hospital.

The spark from the cigarette was a full blaze within seconds, and Stiles was left to stand there and watch as fire consumed the hospital and brought it down within minutes. He knew how stupid it was not to run, the cops and firefighters would be there soon, no way in hell somebody hadn't called 911 by now with the amount of black smoke rising up into the air above him. But he couldn't look away. The heat, even at a distance, was the most powerful thing he had ever experienced. It pressed against him and demanded every ounce of his attention, burning away every other awful thing in his head. 

Even when he heard the sirens, he just stayed where he was and closed his eyes. He heard the shouting as firemen piled out of their trucks and dashed past him, and he heard the sharp voices of what he assumed to be cops yelling at him and ordering him to step back and put his hands on his head. He kept his eyes squeezed shut, but he did everything the cops told him to, he didn't fight them or resist in any way. He was done fighting. Utterly, completely done. 

* * *

"Dad, can you please stop looking at me like that? It's not even that big of a deal," Stiles fiddled with the cord attached to the clunky phone in his hand, and tried to look anywhere but his father's solemn, furious face on the other side of the bulletproof glass. 

"Stiles, if ever something was a big deal, _it's this_ ," his dad spat back at him, while obviously looking Stiles up and down and sizing up his hideous orange jumpsuit and his overall roughed up appearance. "Son," his voice wavered on the word, "I know you think that I hate you, and that I don't give a shit whether or not you're rotting in prison... but you're wrong. I want you out of here and back home with me where you belong. You're my boy." 

"Yeah, right, I'll just hurry on home so we can have some quality father-son bonding time while I watch you get wasted and pass out on the kitchen floor. No thanks. Honestly I prefer prison. At least here they've got a workout room and movie night every second Sunday of the month." Stiles did feel a quick pang of guilt at how truly sad and pathetic his father looked, sitting in his visiting room chair in what were probably the clothes he wore to bed last night, but it passed just as quickly, and he pushed back his own chair and hung up the phone. 

It had been a tense and generally unpleasant few months in the Stilinski home since the fire. 

Unfortunately, there was video surveillance footage of Stiles flicking that cigarette onto the lawn, and any jury would agree (and did, in fact, agree) that Stiles threw it with intent. Even more unfortunate was Stiles' record as a "chronic offender with a history of bad behavior," which qualified him to be tried as an adult. Which, in turn, meant that when the judge found him guilty of second degree arson, he wasn't sentenced to 6 months in juvie, but 10 months in big boy jail. 

So after waiting around his house for two months with nothing to occupy his thoughts besides how fucked he would be (literally) if he dropped the soap, he had been sent to spend a few weeks in the county jail while they "processed" him, and then it was off to the California Correctional Institution, which was a convenient 15 minute drive from his house, which explained why his dad had shown up to say his final goodbyes; anything more than 20 minutes and Stiles knew he wouldn't have bothered. 

So this was finally it. He was being escorted by an armed guard through a pair of double doors and into actual prison. Where he would be sharing living quarters with convicted killers, probably. Stiles may have been a bit of a badass in his own right, but he was still just a 16 year old kid, he used to be an _honor student_ for fuck's sake, how was he supposed to deal with this? 

The guard walked him through a series of almost identical hallways, with white brick walls and unmarked doors, and when they came to the door marked "Cell Block C," the guard turned to Stiles and handed him a nicely folded set of grey sheets, some toilet paper, and a toothbrush. 

"Alright, we're about to enter your cellblock. When we get to your cell, just don't try anything funny and you should be fine. And in about an hour you'll get 20 minutes for breakfast in the mess hall, just follow everyone else when they start to go. Oh, and kid," Stiles stared in shock at the guard who seemed way more friendly than he ought to be, "Don't look anybody in the eye, just look straight ahead, keep your chin up, and don't take any shit from anybody. Got it?" 

Stiles wasn't quite sure what to say, so he just said, "Yep. Got it."

"You're way too young to get mixed up any of this shit, I just hope you're smart enough to stay out of trouble." With a final look that fell somewhere between pity and concern, the guard opened the door, and the calming silence of the hallway was instantly shattered by the jeers and catcalls echoing out of the long row of cells.

"Oh, Jesus," Stiles unconsciously took a step backward, but the guard gave him a little shove, and then he was walking as fast as he could manage without looking like an idiot down the hall, while trying as hard he could to just look straight ahead, and not at the men pressed up against the bars of their cells yelling obscene things at him and in some cases actually reaching through the bars, like they were begging for scraps of food. 

"Is it always like this?" Stiles wondered aloud to the guard as they slowed down in front of a cell containing a rickety bunk bed, an old porcelain sink, and a toilet. 

"Not always. I think they're just excited because you're... Well, you know. Uh, young, and, well, pretty?" The guard now looked extremely uncomfortable, and instead of following up his statement with any sort of apology for calling Stiles pretty, he just unlocked the cell door and stepped aside to make way for Stiles. 

"Okay, well, uh, thanks for the advice, I guess. Bye?" Stiles backed into his cell awkwardly and gave the guard a half-hearted little wave as he walked away. 

He only had about .5 seconds to get a bearing on his surroundings before a bright blob of orange literally fell out of nowhere and landed on top of him. 

“Oh shit, I’m sorry dude,” the blob of orange pushed himself off of Stiles and then held out a hand to help him up. 

“What the hell?” Stiles accepted the hand and pulled himself to his feet. In jail for all of 5 minutes and he was already being assaulted by the other prisoners. 

“I swear I didn’t do that on purpose. I was asleep on the top bunk and I guess I just rolled off the side and... Holy crap, man, how old are you?” Stiles didn’t really think this guy was one to talk, he didn’t look like he could be more than eighteen. He also didn’t really look like he belonged in prison. He had innocent, almost puppy-like eyes and a constant crooked smirk on his face. Despite the fact that he had probably given Stiles a mild concussion, he liked the guy already. 

“I’m sixteen. And my name is Stiles, by the way, in case you were interested. And no offense, dude, but I’d rather not talk about the whole age thing, okay? It’s not a big deal. I was tried as an adult because of my past offenses, blah blah blah, you don’t wanna hear it, I don’t wanna talk about it,” Stiles took a breath and then attempted to end on a less offensive note, “So what’s your name?” 

“Message received, no age questions,” he held up his hands in mock surrender. “I’m Scott, Scott McCall. And don’t worry, I know what you’re thinking, and I haven’t killed anybody. I just robbed a few convenience stores to pay for my mom’s gas and electric bills after she got fired from her job.” Stiles definitely liked this guy. 

“Wow, I feel like I’m being spoiled here. First the guard practically babies me and now my cellmate is a regular Mr. Good Guy. It’s kinda making me wonder about what the rest of this place is like. Do you guys all just hang out and braid each other’s hair?” Stiles sat down on the bottom bunk and plopped down his little pile of necessities. 

Scott laughed, but it had a tinge of sadness to it.

“Unfortunately not. I haven’t met too many other guys in here who are as nice as me. There are a few though, mostly younger guys like us who just caught a bad break. What was it you did, again...? Should I be worried?” Scott sat down on the ground in front of Stiles and crossed his legs Indian-style. It made him look even more adorably childish. 

“I, uh, accidentally burned down a hospital,” Stiles saw Scott’s eyes go as big as saucers and hurried to add, “An abandoned one! It was abandoned, holy shit, no, I did not burn hundreds of sick and elderly people alive, jeez.” 

“Oh, well that’s not even a big deal, then, is it? You accidentally burned down an abandoned building? Who cares?”

“Well, add that to a year-long tirade of shoplifting charges, charges of disturbing the peace, and a few breaking and entering charges, and I guess it’s a big enough deal to land me here,” thinking back on the past year Stiles was almost alarmed at how much he didn’t recognize the boy in his memories, who felt nothing but undirected rage and sadness. The court dates and anticipation of going to jail had been so bracing he’d forgotten to feel sad, and now he almost felt like his old self again. 

He smiled at the thought, and Scott gave him a weird look, but then it was replaced with one of mild excitement when the door to their cell slid open and Scott nearly shouted, “Breakfast!”

“Wow, is that really cause for excitement? I thought prison food was disgusting,” Stiles said as he followed Scott out into the madness of the hall that was filling with hungry inmates. 

“You thought wrong. Honestly, it’s at least twice as good as the stuff they served in my old high school. We get pancakes and juice and everything.”

“Oh. Cool. Awesome, actually, I love pancakes.” Stiles was staring directly at Scott’s face while they walked, because he could practically feel all the eyes on him and he didn’t want to make it worse. 

“Dude, who _doesn’t_ love pancakes? Oh, and this'll be a great time for me to tell you everything you need to know about everyone. Oh, and Stiles?”

“Yeah?”

“Do not, under any circumstances, eat the scrambled eggs.” 

"Got it. Uh, anything else I should know before we get there? Like, life and death kinds of things?"

"Oh, you mean like "never look anyone in the eyes unless you're cruisin' for a bruisin'"?" Scott made a face with his eyebrows all scrunched up and his voice went about 5 octaves deeper in what Stiles assumed was his impression of a prison inmate. Seriously, how was this guy a convicted felon? 

"Yes, exactly that kind of stuff," Stiles looked away from Scott's face for the first time since they left the cell to look around at the mess hall as they entered through the doorway in what had morphed from a disorganized glob of hundreds scattered around in the halls into an orderly line of prisoners. 

"Well actually that staring thing is kind of true, but only with some of the really crazy tough guys. Most people are just trying to get by unnoticed, so they won't start a fight over nothing," Scott handed Stiles a tray and they started to move down the line. This was really just like high school, except with more teardrop tattoos and less bitchy teenage girls. 

"Also, you don't smoke, do you?" Scott asked it flippantly, but for Stiles smoking and cigarettes were sort of sensitive subjects since technically they _were_ the reason he was stuck in prison.

"Uh, not really, I guess, why?" Stiles put his tray down and watched as meticulously rationed amounts of peanut butter, fruit, and sausage links were put on his plate, along with 2 small pancakes. Stiles raised the food up to his nose to stiff it. It actually smelled delicious, and Stiles was beginning to wonder what _was_ the big deal about prison, because so far he liked it better than his real life. 

"Just don't _ever_ accept cigarettes, or anything else for that matter, from _anyone_ , okay? I almost fell for that my first week here. It's just a trick to get you indebted to them. Seriously man, don't do it. Even if it's candy or porn or something, it's not worth eternal servitude," Scott pulled him along again as they made their way through the circular tables, looking for an available spot. It didn't escape Stiles' notice that the seats were attached to the tables, so that, he assumed, nobody could use them to bludgeon another inmate to death. Great. 

Scott finally set his tray down at a table with three other guys who all looked to be relatively normal. Stiles breathed a small internal sigh of relief and set his tray down next to Scott's.

"Hey guys, this is Stiles. He's kinda young, so go easy on him, okay?" The other guys gave brief nods of acknowledgement in Stiles' general direction, but then their attention was quickly drawn back to shoveling food into their mouths. 

"Nice to meet you guys, too," Stiles shrugged and sat down. He popped a grape in his mouth and risked a quick look around at the tables closest to him. Nothing too terrifying, but they definitely looked more like the rough and tough criminal types than the guys at his table, who looked more like underwear models, if Stiles was being honest. 

"So, this is Jackson, and then that's Boyd, he doesn't say much so I wouldn't bother trying to talk to him, and over here is Isaac," Scott smiled goofily in the other boy's direction, and Stiles couldn't tell if that was how Scott treated everybody or if maybe he had a little bit of a thing for this Isaac guy. 

Jackson, being the fastest eater, pushed his tray aside and turned in his seat the face to Stiles. Damn, this guy was attractive. Like, Stiles was having a hard time looking him in the eyes he was so gorgeous. 

"Hey. I'm sure Scott's already filled you in on most of the important things, but I've been here longer than him, and I've seen some stuff. And I feel the need to tell you, what with you being so delicate and all, that you don't want to go getting mixed up with punks, alright? Dudes are gonna be all over you telling you shit like they can offer you protection if you suck their dicks, but you're just gonna end up becoming their bitch, and you _do not_ want that, understand? I'm not usually this friendly but you seem like a nice kid, so I thought I'd give you a heads up," and then Jackson was rising from his seat and walking away, just like that.

"What. The fuck. Why does everyone assume I'm gonna be some guy's girlfriend? I am not comfortable with this stereotype that I seem to have fallen into," Stiles was dead serious, but when he looked around the table the other men were visibly trying to hide their laughter. 

This time it was Isaac who spoke, "Don't pay attention to Jackson, he has a savior complex and a big mouth. Besides, we’ve all had to suck a few dicks, it’s just a fact of life in prison.”

“Ew. Are you serious? Why?” Stiles asked. 

“I dunno. To pass the time? Honestly guys’ll do just about anything to get their rocks off in this place, you’ll learn that pretty soon,” Isaac had finished his food by that point too, so he got up and gave Scott a little wave as he walked away. 

“Well, I’ve gone 16 years without sexual contact, what’s another 10 months? This guy knows what I’m talking about,” Stiles pointed over at Boyd but dropped his hand when he saw the look of utter _un_ amusement on his face. “Whatever man, I was just joking,” Stiles turned back to Scott, who had almost finished his food as well. Stiles realized there was a probably a reason that everybody ate so fast, so he tried to shovel the rest of his meal into his mouth before breakfast time was over. 

“Stiles, chill out. I told you not to bother with Boyd. He’s a cool guy but he literally never says a word and never cracks a smile, so don’t be offended. Also though, for future reference, sex jokes generally don’t go over so well in the slammer. Or, um, any jokes for that matter. Not the greatest senses of humor in here, believe it or not.”

“I can believe it,” Stiles said as he shoved his last sausage into his mouth, and tried not to think of the sexual innuendo and possible foreshadowing that this gesture represented. He muttered, more to himself than anyone, “I am _not_ sucking any dicks,” as they got up and left the mess hall.


	2. Chapter 2

Stiles had spent months mentally preparing himself for prison, and the hell that he would have to endure, but after 78 hours in jail he realized that it had been a total waste of time. 

People were such drama queens! Prison was fine. In fact, it was more than fine, it was great. Stiles had already made a friend, gotten a bit of reading done, eaten some really good food, and today he was finally going to give weight lifting a try. 

He couldn’t remember the last time life had treated him so well. 

Scott wasn’t really into weight training - apparently he was more of a yoga man - so Jackson had agreed to take Stiles out into the “yard” and give him a few pointers. Stiles was painfully aware of the fact that he wasn’t really designed for lifting large heavy objects above his head, but he didn’t want to leave prison with nothing to show for it, and bulking up seemed like the best plan. 

“So I’m thinking we’ll start you on the bars, you can do some chin-ups and if you don’t pass out from exhaustion, then maybe you can try the 30 pound dumbbells...” 

“Hey! I’m not a girl, I can lift more than 30 pounds, okay Jackson? I am _built_ under this jumpsuit. The whole scrawny thing is just an optical illusion,” Stiles couldn’t really help himself from responding cocklily to Jackson’s veiled criticisms of his strength, even though he knew he probably _couldn’t_ do much more than 30 pounds. 

“Yeah, right. Well, either way, just remember the golden rule, because it applies double out there. Remind me what that rule is?”

“Never look at anyone for more than 2 seconds and don’t speak unless spoken to, _sir_!” Stiles knew how much Jackson hated when he didn’t take him seriously, so he made a point to do it as much as possible. Jackson just glared at him and grumbled, “Come on,” while he dragged Stiles through the doors by his collar. 

The yard turned out to be a big fenced in slab of concrete with a few pieces of workout equipment placed haphazardly around it. Jackson has chosen a good time to go, and there were only 6 or 7 other men currently “pumping iron”. 

Stiles _totally_ did not check out the shirtless guy doing sit ups a few feet away from him, because only a gay dude would notice how perfectly muscled and toned that guy was, and how he was making sexy little grunting noises every time he hefted himself up to a sitting position. Stiles was definitely not gay, so of course he didn’t zone out staring at the guy’s perfect abdominal muscles and dreamy blueish green eyes and dark tousled hair and...

“Hey! What the fuck did I just say? No staring,” Jackson actually went so far as to smack Stiles on the back of the head.

“I wasn’t staring! I just... thought I recognized that guy. That’s all. There was nothing else going on there. Nothing at all. So, weights. Chin-ups. Let’s do this,” Stiles said hurriedly, and he stumbled blindly backward to where he thought the bars were located. 

Instead of his outstretched hand colliding with cool metal, he felt something warm and soft; a prison jumpsuit. And upon closer inspection, Stiles realized that there was quite a large and terrifying man inside of that prison jumpsuit, and he was glaring down at Stiles like he had just spit in his face or called him a little sissy girl or some other terrible offense. 

“Oh... Hey. I totally did not mean to do that, man, it was a complete accident and I’m glad you understand and I’m just gonna run away now because...” The massive inmate literally grabbed Stiles by the collar of his jumpsuit and lifted him up so he was at the guy’s eye-level. 

“What the fuck do you think you’re doing, _tonto_?” The guy was clearly a member of the Toros Furiosos, the most feared group of Spanish-speaking badasses in California Correctional. Stiles’ confidence that a prison guard would come and save him before he was beaten to death was starting to waver, and he prayed to whatever deities he could think of that he wouldn’t wet his pants.

“Please. Please don’t kill me. I’m only 16, I haven’t even kissed a girl, come on,” Stiles looked around frantically for Jackson but he couldn’t see him anywhere. Asshole. He probably wanted Stiles to learn a lesson about not following his rules, or something stupid like that. Stiles just sort of flailed around and tried kicking the guy in the balls, but it didn’t seems to have much of an effect. 

Then Stiles heard a powerful voice coming from directly behind him. 

“Hey, why don’t you pick on someone your own size?” Stiles couldn’t stop his body’s natural instinct to roll his eyes, even though he was so relieved that someone was coming to his rescue that he was close to tears. 

The guy holding him up dropped him immediately, and even took a step backwards. Stiles whipped around to see who his savior was, and almost choked on his own tongue when he saw that it was the hot shirtless guy who had been doing sit ups only a moment ago. 

“Seriously, what are you still doing here? Fuck off, and don’t even think about bothering this kid again,” the other man cracked his neck from side to side menacingly, but then huffed an angry sigh and walked back towards the prison in defeat. 

Stiles was aware that he probably looked a little stupid with his mouth hanging open in shock, but his basic motor functions were still a little busted, and there wasn’t anything he could do about it just then. 

“Did he hurt you?” Shirtless guy asked, and Stiles didn’t respond until the other man gave him a small nudge. 

“Oh, um, no. Thanks. For, you know, saving me and everything. But did you _really_ have to use that line? I mean, I haven’t heard someone say that unironically since, well, never,” Stiles regretted the words the second they were out of his mouth, and he was sure that he had just exchanged one beating for another. But the guy actually cracked a smile - barely perceptible of course, but still there. 

“I’ve seen you in the cafeteria,” was apparently the best response this guy could come up with.

“Okay... That’s, creepy?” Stiles was determined to hide the fact that his heart had begun to beat faster and his palms had started to sweat. It wasn’t like he was flattered by this guy basically admitting that he had been watching him in a creepy stalker way, it was just... Well, okay, flattering, that such a gorgeous and intense guy would have taken any notice of Stiles at all. But he was totally not going to let him know that he thought that. 

“I just mean I noticed you because I heard we were getting a sixteen year old kid, and I was curious about you. But you don’t seem nearly as psychotic as I had expected.” 

“Why were you expecting a psycho?”

“It’s no small feat for someone so young to end up here, I just figured you’d be a little more... Intimidating. You seem pretty normal, at least by this place’s standards,” shirtless guy reached for a crumpled tank top on the ground and pulled it over his head, leaving Stiles with nothing to refer to him as in his head, because he was no longer shirtless. 

“So what’s your name? I know I’m not supposed to ask people that, but I figured since you saved me and all that you won’t kill me for asking,” Stiles saw the guards starting to herd the prisoners back inside, and he didn’t want to leave without finding out this guy’s name. 

“Derek. And you’re Stiles, right? Is that your real name?”

“Nope,” and then they were being physically pulled in different directions by the guards, who weren’t normally this hostile but got irritated when people didn’t move as quickly as they wanted. 

Stiles looked over his shoulder to get a last look at Derek, and was surprised to see that he was looking right back at him. He pulled another not-quite-there smile, and then he was gone. 

Stiles made a decision then and there to learn every single thing he could about Derek, starting with his last name.


	3. Chapter 3

“Heeeey Scott,” Stiles sing-songed innocently as he plopped down next to him on the sad excuse for a couch that made up most of what was referred to as the “dorm area”. 

“What do you want?” Scott didn’t ask it in a mean way, but more of a “I’m not a total idiot and I can tell when you’re going to ask me for a favor” way. 

“What? Who says I want something? Can’t a guy just spend some time with his pal without an ulterior motive?” Scott just raised his eyebrows while keeping his eyes on the book he was reading. “Alright fine, I do need something. Just some information on this guy. Uh, Derek, I believe his name was...”

“Derek _Hale_?” Scott’s attention was now fully shifted to Stiles. 

“I dunno, that’s what I was gonna ask you. Kind of a tall dude, furrowed brow, eyes like the sea after a storm?” Stiles really hoped that Scott could detect his sarcasm for that last part.

“Uhh, well the only Derek I know of is Derek Hale, and he’s pretty much the most terrifying guy I have ever met and you should avoid him at all costs. _Why_ are you trying to learn about him?” Scott’s face was scrunched up in confusion as he pondered his own question. It was kind of adorable. 

“Nothing. No reason. Never mind. I guess I’ll see you later-” Stiles tried to make a run for it but Scott jumped up and blocked his way. 

“I’m serious, Stiles. Even the _really_ hardcore guys are afraid of him. I don’t really know why, it’s just like an unspoken thing that everyone avoids him. Nobody even knows what he’s in here for.”

“Scott, relax. I was just curious about him because I thought his tattoo was cool. I promise to never ever ever go near him or interact with him in any way,” that seemed to calm Scott down a bit, and he smiled and sat back down with his book. Stiles mentally patted himself on the back for coming up with an excuse as quickly as he did. He definitely _had_ noticed Derek’s fascinating swirly tattoo between his shoulder blades, but it was far from the reason he was interested in learning about him. It was more that he wanted to know his motivation for putting his own ass on the line to save a kid he had never even spoken to before. 

Stiles knew from a conversation he had overheard between Isaac and Jackson that there was nothing you couldn’t get in prison in exchange for a carton of cigarettes, and that included information. The only problem was, Stiles did not have a carton of cigarettes. Stiles didn’t really have anything, except for, apparently, his understated good looks and delicate bone structure which made everyone assume he was down to party in a deeply un-heterosexual way. And since Stiles was not keen on the idea of using his newfound status as sexually desirable to get information from terrifying criminals, he was at a loss for what to do next in his Derek Hale fact-finding mission. 

“Hey!” Someone yelled from behind him. Stiles whipped around so fast he very nearly tripped on the too-long pant legs of his jumpsuit and fell flat on his face. It was Isaac who had done the yelling, and as he jogged up beside him Stiles could tell he was out of breath, like he had been running all over the prison. 

“Stiles, have you seen Scott? I wanted to tell him something. Important.” Isaac leaned over and placed his hands on his knees, trying to catch his breath. 

“Why are you so out of breath? Did you just finish running a 5K or something?” Isaac stood up and looked down at the floor sheepishly. 

“I just really wanted to find Scott, and when I didn’t find him in the library or out in the yard I guess I sort of overreacted and... started running?” Isaac looked so embarrassed that Stiles really couldn’t bear to give him any more shit about it, but he was now officially convinced that Isaac and Scott had some sort of weird love connection going on. 

“Uh, anyways, if you see Scott, can you just tell him-”  


“Tell me what?” Scott strolled up behind Isaac and clapped a hand on his back.  


“Oh, hey Scott,” Stiles watched as Isaac’s whole demeanour completely changed before his eyes, and the most ridiculously goofy smile spread across his face. Stiles just raised his eyebrows slightly and didn’t say anything, but he felt he had a responsibility to Scott to tell him how _not_ subtle they were being. 

“I just wanted to let you know that the guys from Cell Block A were planning on having a little poker game tonight, and I know how much you love card games,” Isaac said. 

“Woah, how’re they planning on getting away with _that_? The guards are usually so strict about gambling...” Even as he started worrying out loud, it was obvious from the light in his eyes that Scott was excited. 

“When have rules ever stopped these guys? Anyway, the buy-in is one pack of cigarettes, and I have some extras if you don’t have any,” Isaac was completely ignoring Stiles by this point, but Stiles’ ears perked up at the mention of the currency of the realm. 

“Isaac, any chance I could get in on this action? I really need some cigarettes. Y’know, cravings are a bitch and whatnot.”

“Stiles, I thought you didn’t smoke?” Scott asked, looking slightly concerned. 

“Right. Well, I wanna start.”

“I can’t just give these things away, but if you want to play tonight and give me some of whatever you win, then I guess I can help you out,” Stiles had never played a single hand of poker in his life, but he had nothing to lose and also the boredom had started to set in, so he was desperate for something to do.

“Sounds cool, I guess I’ll see you guys later.” He headed in the direction of the library on the off chance that they had any books on card game strategy. Stiles had a bad feeling that his poker face was going to be complete shit. 

* * *

Stiles was anxious. 

He wasn’t sure if it was due to the fact that he was currently sandwiched between two of the largest, scariest men he had ever seen, the way every man in the room seemed to be leering at him, or the fact that they were breaking one of the prison’s biggest rules by gambling in a secret room that seemed to have been carved out of the wall with homemade shanks (Stiles wasn’t sure about that last part, but he felt it was safe to assume based on the fact that the floor, walls, and ceiling were made of dirt and crumbling mortar, and the only light in the room was emanating from the lit cigarette butts glowing in the mouths of the other men). 

He had gotten separated from Scott and Isaac when they very inconsiderately decided that they would prefer to play at the “more advanced” table, leaving Stiles with a single pack of Marlboro’s and absolutely no idea what he was doing. Scott had done a brief rundown of how these types of things usually went down, mostly just about how rare it was that they were able to sneak large groups of inmates into these secret rooms without getting caught. Stiles was coming to realize that he had landed himself in a pretty shitty prison if the prisoners were able to get away with as much as they did, but he wasn’t complaining.

So far he had managed to bullshit his way through one hand, just picking up the rules as he went along, but he didn’t know how much longer he could pretend that he wasn’t terrified and confused beyond measure. He couldn’t even remember why he had thought this was a good idea in the first place. 

The surly gentleman with the skull and crossbones tattoo who was acting as dealer cleared his throat loudly to signal that the second hand was about to begin. 

“Alright boys, this round’s blind is 3 smokes, unless you’ve got something else you’d like to offer up instead...” The dealer looked straight at Stiles and grinned, baring every one of his jagged yellow teeth, and Stiles was pretty sure he didn’t imagine every other pair of eyes giving him a creepy once-over after that line, and he quickly threw his 3 cigarettes down on the table. 

“That’s too bad, but we’ll see if you don’t reconsider once you’re all out of smokes and your only bargaining chip is that sweet little ass...”

“ _Woah_! Oh my god, okay, I’m out. I quit, or whatever you call it in poker. This is so not cool,” Stiles stood up but was immediately yanked back down by the guys seated on either side of him. 

“You can’t quit a prison poker game, princess, that’s the whole idea. High stakes,” the six other men laughed at that, but Stiles was struggling not to wet his pants. He had no doubt that he’d be out of cigarettes within the next two hands, possibly sooner, and he had no idea how to get out of this unscathed. 

He reached out for the two cards which had been dealt to him, being extremely careful to hide them from the others. He had two Jacks. He didn’t know if that was really good or really bad, so it wasn’t difficult for him to keep his expression blank. The man to his right threw down an additional 4 cigarettes, and then sat back and smirked. Stiles stared down at his remaining cigarettes; there were only 5 left. He fiddled with then, twirling them around in his hand absentmindedly while he tried to remember what he should do in this situation. 

“You should call,” a voice whispered from behind him, so close he could actually feel the words on the back of his neck. He looked over his shoulder and right into the eyes of his mysterious savior, Derek Hale. Stiles couldn’t help but smile with relief. 

“You’re saving my ass _again_? What are you, my guardian angel?” Stiles whispered back, as he called the other man’s 4 cigarettes and turned back around towards Derek, who was crouching leisurely on the floor behind him. 

“No, I just know how tough it can be for pretty guys like you in prison, and I thought since it was obvious you couldn’t protect yourself, I’d do it for you,” Derek grinned in a way that suggested he was just kidding, but Stiles’ ego was still a little bruised. He opened his mouth to respond with something about how he certainly could take care of himself, thank you very much, but what came out instead was, “You think I’m pretty?” 

Derek laughed softly at that. But instead of answering, he just slipped another pack of cigarettes in the pocket of Stiles’ jumpsuit and stood up and left, just like that. Stiles watched him go, and he couldn’t help but admire the way Derek’s ass looked in his jumpsuit, the way the fabric was stretched so tightly over his perfectly rounded-

“Hey! We have a little game here that we’d like to get back to, if you wouldn’t mind, princess.” Stiles snapped out of his undeniably ass-themed daydreams to place another bet, but his mind was no longer focused on the game. 

His thoughts were racing a mile a minute, and he was confused about everything that had just happened, but mainly why whenever he thought about Derek his dick got sort of hard and he thought about kissing him and snuggling up into his broad chest and how nice he smelled and why was Stiles so gay all of a sudden?


	4. Chapter 4

Somehow the rest of the night went off without a hitch, and Stiles walked away from the poker table 10 cigarettes and 2 pieces of hard candy richer. The candy was a nice surprise, and it was probably one of the least surprising items that some of the other men offered up instead of cigarettes (a packet of ramen noodles, a glow in the dark condom, and a ball of multi-colored rubber bands were among the more random items exchanged at the table). 

Unfortunately, more information on Derek was not one of the things Stiles gained from his evening of forbidden gambling. All he knew about Derek was that he seemed to have some sort of soft spot for Stiles and followed him around so that he could pop up at opportune moments and help Stiles out of sticky situations. 

Stiles decided to put a hold on his investigation for the time being, mainly because he realized he didn’t care _why_ Derek was so interested in him, just that he _was_. Also he was getting nowhere, and most people seemed too afraid of Derek to risk talking about him, which still made absolutely no sense to Stiles, unless they were afraid of being eye-fucked to death. Seriously, Derek’s penetrating stares could calm a wild beast, at least from what Stiles had seen of them. He just assumed that most other people didn’t get to see the softer side of Derek Hale, the one that involved smiling or humor or any semblance of being who he was around Stiles. 

Stiles had heard some pretty hard to believe stories from the guys, namely Jackson, about how Derek normally behaved himself, but he chose to ignore them because a.) Jackson tended to exaggerate and b.) lots of people were mean to Jackson, he just sort of inspired animosity, so if Derek had shoved him in the hall or something, it was probably Jackson’s own fault. 

Stiles was still musing on the many flaws of Jackson’s personality when the bus that was taking the inmates to their stretch of litter-covered highway pulled to a stop on the side of the road. Stiles had already experienced many of the “rehabilitation activities” that the jail forced them to do almost every day, but the oh so clichéd picking up of trash on the side of the highway was a new one. 

Stiles shuffled slowly off the bus and into the sweltering midday sun. His ankles were attached with thick plastic cuffs, but his hands had been left free so he could spear soda cans and candy wrappers with a big stick. He sighed dramatically when the guard handed him his trash bag and poker and pointed over to where Isaac, Scott, Boyd, Jackson, and another man that Stiles didn’t know, were already working. 

“How goes the litter patrol?” Stiles asked as he snuck up between Isaac and Scott and put his arms around their shoulders. He was really just using the vantage point to crane his neck around and look for Derek, but he was nowhere among the 40 or so other men working that day. Stiles shrugged almost imperceptibly and got to work making California a cleaner place, but it wasn’t long before he was distracted again. 

“So, what’s your story, man? You’re new, right?” Scott had started making conversation with the mysterious newcomer, and the rest of the guys seemed to have stopped working too, so Stiles thought it couldn’t hurt to get in on the conversation if everyone else was doing it. Some of the wardens could be extremely strict with talking on the job, but Stiles had seen the guard from his first day who had been nice to him was among the bunch today, so he hoped they wouldn’t get a verbal lashing for taking a little break. 

“Uh, yeah, the name’s Danny. I thought you weren’t supposed to talk about what you were in for? Isn’t that like, jail rule number one?” The guy seemed friendly enough, and he was definitely easy on the eyes, but Stiles wasn’t sure if he liked him just yet. 

“Oh, you don’t need to worry about that with us, we’re all normal. Or, at least, we’re not gonna beat you up or anything. But it’s cool if you don’t want to talk about it,” Scott had a way with people, though, and Danny smiled at the friendly exchange and went on.

“Okay. Um, it was drugs. Coke. I wasn’t into it or anything, but I got involved in some bad shit, dealing and stuff. Judge only gave me 3 years, but it still blows. My boyfriend was more devastated than I was, though. Hopefully he’ll visit me at some point, but I’ve heard the conjugal trailers here are pretty crappy,” Stiles couldn’t help but perk up at the mention of the word “boyfriend.” He was starting think he might like this guy after all, or at least he might be able to ask him some questions about his recent... confusing feelings. 

“It’s all true. My girl Lydia came to see me once, and-” Jackson was cut off by a chorus of loud groans from Scott, Boyd, and Isaac. 

“Do not get him started on Lydia, for the love of all that is holy,” Isaac said. 

“C’mon guys, it’s not like I talk about her _that_ much, I just-”

“Ah ah ah! No. Shh. We already know that she’s so smart, and so hot, and she smells like roses, and gives “the best head on the West coast,” you can seriously save it,” Jackson only looked mildly affronted, like he knew that he did in fact talk about her too much, but because Stiles loved playing the devil’s advocate, he just had to ask.

“Who’s Lydia? _I’ve_ never heard of her before,” He grinned at the second round of miserable groans. Jackson seemed all too delighted to share the story of his beloved girlfriend, who it turned out was the reason he had been sent to jail in the first place. He launched off on a tale of romance and jealously and sex, there was really quite a lot of sex in this story, and it culminated with Jackson almost beating the life out of some guy who has tried to come on to Lydia at a bowling alley. He had been charged with assault and battery and gotten 6 years, 4 of which he had already completed. Stiles couldn’t imagine being stuck in one place for so long, and took a moment to count his relative blessings that he only had 9 months left in the slammer. 

“Alright guys, back to work, you’re lucky it’s me and not Gerard, you know how much worse that would be,” the guard from Stiles’ first day had walked over at some point during Jackson’s story. Stiles wanted to say something to the man who had shown him so much kindness, but he wasn’t sure if it was smart to look friendly with a guard. He decided to say something anyways. 

“Hey! It’s you. Nice guard man. I just wanted to say thank you, for, you know, being nice-”

“Stiles, good to see you in one piece. I take it California Correctional is treating you well enough?” The guard smiled back at him. 

“Yeah, you know, considering. What’s your name, just for future reference, if I ever need a favor or anything, I’ll know who to go to,” Stiles winced inwardly the second he said it. He hadn’t meant to sound spoiled or anything, he just wanted to know his name so he could have a sense of security, that someone with a little bit of power was watching over him. 

“It’s Chris. Argent, not to be confused with Gerard Argent. Y’know, the warden? He’s a real hardass, and I can say that because he’s my dad. Just stay off his radar if you can avoid it, alright? I’m sure your friends here would tell you the same,” with that last bit of foreboding advice he started making his way back towards his post near the bus. 

“Gerard... That old guy? Wow, that’s his dad? It’s kind of weird that they both work at the same place,” Stiles said. 

“Yeah, I guess. I think Chris just likes to be able to look after his dad, make sure he doesn’t do anything too crazy,” Scott said. 

“I’m bored of this conversation, can we get back to talking about me?” Jackson whined. Boyd laughed and punched him playfully in the arm, but shook his head and went back to working. “We can talk about something else. What about how much we miss sex?”

“Why would we _want_ to talk about that? Are you insane? Don’t make it any worse for us,” Danny laughed, but it was clear that the rest of the men had no problem with the topic change. They launched into a heated and really quite alarmingly vulgar discussion about which of their past conquests had been hotter, and how much they all missed “the smell of a woman”. It made Stiles squirm uncomfortably, as he had yet to have a sexual experience with anyone besides himself and his own right hand. 

“What about you, Stiles? How long has it been since your last time?” Isaac asked, and Stiles looked up from his work to see every pair of eyes trained directly at him. 

“Uh. Um. Not too long. You know. A, uh, regular amount of time, definitely,” Stiles felt a blush creeping up his neck and tried to look like he was too focused on the cheetos bag he was attempting to spear to continue in the conversation, but the stunned silence around him indicated he had not been successful. 

“No shit, he’s a goddamn virgin,” Boyd stated to no one in particular. 

“Seriously man, you better not let that slip to anyone else, you’re already like catnip to these guys,” Isaac said solemnly, giving Stiles a look of genuine concern. 

“Yeah, I had actually noticed that, thanks,” Stiles managed to say before basically tripping over his own feet in his haste to get away from the most embarrassing conversation of his life. 

He scanned the barren desert highway for another group of promising individuals, but unsurprisingly he couldn’t spot a single person who didn’t look like they would enjoy eating him for lunch. 

He caught sight of the old warden, Gerard, screaming with such intensity at an inmate that his face had turned honest to God purple, and quickly turned in the opposite direction. Stiles had enough to be wary of without adding psycho power crazed warden to the list. 

“Hey, kid, can you help me out over here?” A smooth, pleasant voice caught Stiles’ attention from behind a grouping of shrubs on a nearby hill. Stiles couldn’t even see the man who had spoken from his position on the flat part of the road, so he inched towards the bushes with extreme caution. 

“Uhh, hello?” He poked his head around the side of the outcropping and saw a relatively unthreatening inmate with sandy blonde hair struggling to free himself from what looked like a rabbit trap. 

“Oh, shit! Are you okay? Do you need me to get someone?” Stiles moved as quickly as his plastic foot cuffs would allow and dropped down beside rabbit trap guy. 

“No, just hold this part here, and I should be able to get it open,” the man said with frankly amazing calmness considering Stiles could see blood oozing liberally from his calf. 

“Okay, got it,” Stiles gripped the rusted metal of the trap and squeezed his eyes closed as the man wrenched the contraption open far enough to move his leg to safety. 

“Woah! That was intense, are you okay?” Stiles helped the other inmate to his feet, and then backed away a few paces just to be safe. Even though he just helped save this guy, he could still very well be a crazy killer. 

“I’m as well as can be expected. On the bright side, at least now I’ll get to spend a few days in the infirmary,” there was something off about the calmness in his tone, and Stiles found himself inching even further away. 

“Well that’s good. Find the silver lining and whatnot. Really though, um, you are bleeding a lot. I should get one of the wardens to take a look at your leg,” Stiles turned to go, but the man just kept talking in his smooth, frightening monotone. 

“You’re the Stilinski boy, aren’t you? I’ve already heard so much about you, and it’s only your what, seventh day here? You sure do make an impression. I was talking to Derek just the other day about how-”

“Huh? Derek? Derek Hale? Do you know him?” Stiles’ sense of self preservation wavered for just long enough that the other man was able to saunter right up behind him and place a strong hand on his shoulder. 

“Yes, I know Derek quite well. You could even say we’re like family. Oh, the things I could tell you about Derek...” Stiles was so completely torn between his burning curiosity and his paralyzing fear that he stayed rooted to the spot, waiting for the man to say something else. 

“Yeah? Like what?” 

“Hmm, before I tell you anything, I’d like to know what you’ll do for me in return for this valuable information,” Stiles ducked out of the man’s grip after that clearly sexual remark, and turned to face him from a safe five feet away. 

“What, besides literally saving you from the jaws of death? No, dude, just... No. Tell Derek he’s a secretive weirdo and if he wants to keep saving me from shit, he should at least have a proper conversation with me first,” Stiles spat back at - “What’s your name, anyway?” “Peter” - at Peter, before hurrying back to find Scott and the others. 

What a weird fucking afternoon. 

* * * 

“I don’t think this will ever not make me extremely uncomfortable,” Stiles remarked as he stripped out of his filthy jumpsuit along with 50 other men in preparation for the dreaded prison shower. 

“You think that now but... No, you know what, this part never really gets better,” Scott shrugged as he peeled off his own sweaty undershirt and tossed it into a locker. 

“As if I didn’t already feel enough like a choice cut of meat in a butcher shop window, being naked in front all of these sex-crazed maniacs is about 1,000 times worse than normal,” Stiles glared at Scott’s badly concealed laughter, and just grabbed his towel and soap and made his way into the shower area. 

The room itself was big, slippery, poorly-lit, and smelled of mildew and fear. It was every bit the prison shower scene cliche, except luckily the men seemed much more interested in getting themselves clean and out of there than sexually assaulting each other, as the movies would have you believe. 

Stiles tried really hard - wait, no, wrong choice of words - he tried his best not to peek at what was going on below the belt with the other dudes, which in most cases was easy because a lot of the prisoners were either old or had gross bodies, but sometimes his eyes slipped south of the border and that was problematic for him in a number of ways. Namely because he had been experiencing some confusing feelings as far as his sexuality recently, and he had to focus very intently on _not_ getting a boner when he was crammed against this many soaped up, muscley guys because otherwise he was pretty sure he’d get beaten up faster than you could say-

“Oh great, Derek Hale just walked in.” 

Shit. 

Stiles froze mid-shampoo at the words that had just left Scott’s mouth, and he tried to remain calm as he saw Derek out of the corner of his eye strutting past in all his fantastically naked glory. Shit shit shit _shit_. 

“Yuck, that guy is just, bad, he’s so, frowny, and uh, quiet,” Stiles tried to think of any other negative adjectives to describe him but Scott was clearly not scrutinizing his response as much as Stiles thought, because he was already turning off his shower nozzle and heading for the exit. 

“See ya,” Scott waved over his shoulder, and Stiles noticed with a sense of creeping dread that there seemed to be a mass exodus of prisoners from the shower upon the arrival of Derek Hale, and it looked as though he would soon be alone with him if he didn’t do something about it. 

Stiles attempted to continue soaping himself up without looking over his shoulder, but he could feel Derek staring at him. The skin on the back of his neck started to get all hot and prickly and he quickly decided against playing it cool when he turned around to see that Derek was literally the only other person left in the room, and he was sporting a very noticeable erection and fuck Stiles was not equipped to handle this at all. He made a small squealing sound of distress and bolted from the showers, still half covered in soap, before Derek could say anything to him. 

* * *

So far, the worst thing about prison had to be how much time Stiles had alone with his thoughts. He appreciated the guards’ attempts to keep the inmates busy, even when they were doing disgusting or degrading menial jobs, because anything was better than laying in his bunk, counting the cracks in the ceiling and thinking about his old life. 

His thoughts often drifted to the days before his mom got sick, when his biggest problems were controlling his ADHD and getting to the next level on Kingdom Hearts. He missed his friends, who he hadn’t seen in over a year since alienating them in favor of the thugs who were by his side throughout his self destructive crime spree. 

And of course he missed his mom, but even worse was how much he missed the person his father used to be. His dad was his best friend when he was a kid, and he had always looked up to him more than anyone else. Now he felt like he could barely recognize him, and Stiles knew his stint in prison would hardly do anything to better his dad’s current emotional state. 

“Scott, I’m going to see if they need anyone on kitchen duty, you good?” Stiles swung his legs off the mattress and moved to signal to the guard that he wanted to leave the cell.

“Mmmph. I’m sleeping. Go away,” Scott grumbled from the top bunk. 

Stiles just needed to take a walk to clear his head, and he was eternally grateful that the guards pretty much let them do whatever they wanted, because the security level was so low. 

Once he was loose in the hallway, Stiles set about trying to think about anything besides his walk down painful memory lane. He tried to focus on how good Derek had looked in the shower the other day, but before he had time to get a good fantasy going, he was rudely distracted by a commotion in one of the guard’s stations. 

He looked around and didn’t see anyone else in the immediate vicinity, so he sauntered up to the door and slowly peeked through the tinted window. All he could make out was that there were two men, one definitely looked like Gerard, and the other was an inmate, but Stiles couldn’t quite make out his face. They looked like they were talking calmly, and there was no indication of what the commotion could have been. Stiles jumped back with a start when Gerard turned to face the door, and he booked it across the hall to crouch behind a janitor’s cart. 

“...You just don’t let it happen again. I need the next shipment no later than Friday, you got that, boy?” Stiles heard Gerard saying to the inmate. 

“Yes, sir. I’m sorry about today, my supplier got into some trouble with the mob...” Stiles clapped a hand over his mouth to hide the involuntary gasp of surprise when he heard Danny, the sweet new guy, respond. 

Stiles peeked over the top of the cart, his head obscured by a dirty mop, to try to see exactly what was happening. He could see Gerard slip a roll of what looked like hundred dollar bills into Danny’s pocket before walking away towards the East Wing of the prison. 

“Holy shit,” Stiles swore under his breath. He waited a few minutes after Danny had left too before jumping up, running off in search of someone to tell about this new discovery. 

He couldn’t go back to his cell block until 7:30 because he was supposed to be on a kitchen shift, so he went to the only other place he thought he might find someone who would care about his tale of corruption.

When he burst through the doors, every head in the room snapped up to glare at him. 

“Sorry, I’ll be quiet, I swear, sorry,” Stiles whispered to everyone at once, as he slipped into the stacks to see if Jackson, Isaac, or Boyd were anywhere around. 

He came to an abrupt stop when he turned a corner and found Derek sitting at one of the small wooden desks, his head buried in a beat up copy of _Moby Dick_. 

“Ahem,” Stiles cleared his throat loudly, and Derek raised his head from his reading slowly, his eyes getting almost imperceptibly wider when he saw who was standing in front of him. 

“Hello...?” Derek replied, quirking one of his massive eyebrows up in amusement. 

“Yeah. Hello is right, you big, broody, secretive... guy,” Stiles sat down in the chair next to Derek and faced him head on, trying to give him an expression resembling “I’m done trying to figure out your mysterious shit” but in reality probably looked more like he was experiencing brain freeze. 

“Did you want my _Moby Dick_?” Derek asked with a smirk, like he was God’s gift to slightly dirty puns. Please. Stiles was not having any of his flirtatious banter, and he grabbed the book from Derek’s hand and slammed it shut on the desk. 

“No! Geez! What is with you? I actually have something serious to talk about, but if you’re going to act like a middle schooler, you can forget it,” Stiles huffed. 

“Says the sixteen year old,” Derek muttered back, looking like he was quite enjoying getting Stiles riled up. 

“Do you wanna hear my tale of power, drugs, and corruption, or not?” Stiles all but yelped back at him. That seemed to sober Derek up, if only marginally. 

“What did you see?” 

“Gerard Argent giving that guy Danny a huge roll of dirty drug money,” Stiles said, huffing out an exasperated sigh when Derek didn’t react with immediate surprise and outrage. “For drugs!” Stiles tried again. 

“Stiles, how do you know that’s what you saw? It doesn’t sound like you actually saw any hard evidence,” Derek said. 

“I know what I saw, and I heard them say something about a dealer or a shipment or - or _something_ , I mean, come on, this is some messed up shit, right?” 

Derek leaned back in the creaky library chair and dragged a hand over his mouth, seemingly deep in thought. 

“If you’re right, and we help expose a secret drug operation spearheaded by the most senior warden in this place, it could be very good for us. We might get significant time shaved off of our sentences-” Derek seemed to actually be interested in this now, and Stiles spared a quick moment to wonder not for the first time just how bad Derek’s sentence was, and what he had done to get it. 

“We should talk to my uncle, he generally knows about all the seedy shit going on beneath the radar around here,” Derek rose from his seat, and signalled for Stiles to follow him. 

“You and your uncle are inmates in the same prison?” Stiles laughed without thinking, and Derek rewarded him with an irritated glare. 

“I guess it runs in the family,” Derek snapped back at him.

“Whatever, dude, I just hope he knows what he’s talking about. I would _love_ to get out of here a few months early. I’ve got a Venus flytrap at home that desperately needs watering.” 

Derek just rolled his eyes at that, and Stiles wasn’t sure if it would be presumptuous to say the look Derek gave him was close to _fond_. 

“Okay, we’re here. You should let me do the talking, he can sometimes be a bit... much,” Derek pushed open the door to the closed-for-repairs bathroom they were standing by, and Stiles followed behind him, deciding not to ask any stupid questions like “ _Why the hell are we in a dirty old bathroom?_ ”. 

Derek walked with purpose towards the last stall on the left, and then he entered it and closed the door swiftly behind him. 

“Uh, alright. I guess I’ll just wait here,” Stiles said, but Derek was already opening the door back up to signal for Stiles to join him. 

“Not that I’m complaining, but won’t it be a little cramped in there? Also, what are we doing, is your uncle some sort of toilet monster? I-” Derek opted for the non-verbal approach to explaining the situation and grabbed Stiles by his collar to drag him into the stall. The display of his manly masculine strength totally _did not_ turn Stiles on at all, by the way. 

Stiles’ jaw actually dropped at what he saw once inside the stall. An entire wall was missing, and within the carved out space was a whole array of contraband items, a desk, a sofa, as well as a pile of what looked like different official uniforms from various occupations within the prison. But the real reason for Stiles’ surprise was the man sitting behind the desk, eerie smirk firmly in place, with his hands steepled together and resting on the desk. 

“You!” Stiles exclaimed, but Peter just rolled his eyes (Stiles’ assumed that constant annoyance and snark ran in the family too) and turned his attention to Derek. 

“How can I be of assistance to my favorite nephew on this fine day?” Peter asked. 

“Stiles saw something go down between Argent and the new guy, we wanted to know if you had any info on a possible drug ring-”

“‘ _We_ wanted to know’? I guess you’ve finally made a friend after all this time. Seems a bit of a darkly ironic choice though, wouldn’t you say?” Derek and Stiles both stared at Peter with total confusion. 

“Well, the arsonist and the man who lost most of his family in a fire? No? Am I the only one who thinks it’s a bit strange?” Derek recoiled from Stiles’ side the instant the word “arsonist” left Peter’s lips, and Stiles felt a stab of irrational panic in his gut at the thought of Derek never speaking to him again. 

“Hey, Derek, no, it’s not that bad, it was an accident, really, I-” Derek shoved past him and bolted from the bathroom, a scowl of pure disgust marring his handsome features. 

“Why the fuck would you say that to him?” Stiles shot back at Peter, who looked terribly pleased with himself. 

“You know what? I don’t care why,” Stiles shrugged and then, throwing all caution to the wind, punched Peter right in his ugly, smug face. 

“Oh! He’s got some fight in him after all, I like it!” Peter shouted after Stiles, but he was already out the door and running back towards the library to try to find Derek and explain himself.


	5. Chapter 5

The lights were off and the library was deserted by the time Stiles made his way back. He had no idea if this was where Derek had run off to, but he couldn’t really think of where else he would go. 

Stiles’ head was racing and his heart was hammering in his ears, the rush of new information about Derek almost too much to process at once. The encounter with Peter had been a blur, but Stiles knew he would never forget the look on Derek’s face when he found out what Stiles had done. It had knocked the breath out of him to see Derek look so utterly betrayed and hurt, and Stiles knew it was _beyond_ important that he found him as soon as possible and explained himself. 

He walked gingerly through the rows of books, trying to keep his steps as light as possible so he wouldn’t scare Derek off if he was in fact hiding in the stacks. 

It was difficult to see in the low light, and Stiles’ eyes had yet to fully adjust to the darkness, but even among the shadows he was able to clearly spot the bright orange of Derek’s jumpsuit, hidden away in the furthest corner of the library.

He froze instantly, realizing that he hadn’t really thought further ahead than finding Derek, and now he had no idea what to say to him. He walked slowly towards where Derek was sitting on the ground, head in his hands, but stopped when he noticed the way Derek’s shoulders were shaking, almost like he was-

“Oh my God, are you _crying_?” Stiles knew that was probably one of the worst things he could have said, but the shock of seeing the ever stoic and menacing Derek Hale in tears was just too much for him _not_ to comment on it. 

A small part of him had been hoping that Derek would lift his head, roll his eyes at Stiles, and berate him for even suggesting such a thing. But when he did look up at him, his eyes were rimmed with red and his cheeks were shiny with tears, and he looked more pathetic and helpless than anything Stiles had ever seen, and he’d seen his mother die slowly from a disease that practically ate her from the inside out. 

Derek didn’t say anything, just looked at Stiles for a brief moment before dropping his head back down between his knees. Stiles sighed and sat down in front of him, briefly considering placing a hand on Derek’s shoulder before realizing how monumentally stupid that would be. 

“Okay, you don’t wanna talk to me? That’s fine, just listen,” Stiles took a deep breath and steeled himself to reach into the darker corners of his memories where he usually tried so desperately to avoid. Maybe if Derek knew his story, he would feel safer opening up about his own. 

“I don’t know exactly what happened to you, or your family,” Stiles flinched at the way Derek’s shoulders tensed up at even the mention of them, “but I do know how it feels. To lose someone. To feel like a huge chunk of your heart was ripped out and to feel that loss every single day like it’s brand new. My mom was my best friend, and when she died I kind of… lost it. Went nuts, started acting like nothing in the world mattered and like I could do whatever the fuck I wanted,” Stiles was gauging Derek’s reactions carefully, and it seemed like at the very least, he was paying attention to what Stiles was saying. 

“I did all that cliche delinquent shit. Shoplifting, drinking, vandalism, all of it. Derek, I just wanted to numb the pain of losing her, do you get that?” Derek shifted so that just his eyes were visible over the tops of his folded arms, now free of tears but clearly still full of anger and uncertainty. Stiles kept going. 

“I smoked a lot too. And that’s all it was. That’s _all it was_ , okay? I was smoking a cigarette and I threw the butt onto some grass, one thing led to another, then the abandoned hospital was going up in smoke. I’m not a fucking - what is it even called-”

“Arsonist,” Derek said. 

“Yeah, that. I’m not an arsonist, I’m just extraordinarily unlucky. Alright?” Stiles looked hesitantly at Derek, who was sitting up normally again, a bit of the tension gone from his stiff and icy demeanor. 

“Alright,” Derek said, seeming to finally deflate as he leaned back against the bookcase. 

Stiles wasn’t sure what the best course of action was with Derek in this delicate state, but he just had to know, so he scooched even closer to Derek and finally worked up the courage to lay what he hoped was a comforting hand on his shoulder. 

“What happened to them, Derek?” Stiles asked softly, crossing his fingers behind his back for Derek to not lose his shit again. 

Derek leaned his head back against the books and closed his eyes, and after almost a minute of silence had passed, he opened them again, meeting Stiles’ eyes in an intense but not unfriendly stare. 

“Her name was Kate Argent. When I was 15 she came into the shoe store where I worked and made it her personal mission to torment me. She was a lot older than me, but she was gorgeous, and she knew it. She would come in once, sometimes twice a week, always wearing these ridiculously skimpy outfits and flirting with me like she didn’t know how to do anything else,” Stiles had no idea how any of this tied in with the death of Derek’s family, but he knew he wouldn’t like it. 

“I was a 15 year old kid, and she was sexy and exciting and interested in me. So naturally I became… infatuated with her,” Derek looked away from Stiles, a clear tell that he was attempting to hide something. 

“You loved her,” Stiles said, with no hint of a question. Derek nodded. 

“And she loved me. But in the end, that was the problem. She started showing up at my house every day, even though we both knew our relationship had to be kept a secret or else she would go to jail. She would call me literally 50 times a day, demanding to know where I was. There was one time when I got home from school and found her lying naked in my bed, even though my parents were both home. I guess I should have known something was wrong then, but I didn’t want to see it…” Derek looked like he might start crying again, so Stiles reached out and hesitantly cupped a hand on the side of Derek’s jaw, lifting his face so he could meet his eyes. 

“See what, Derek? What did she do?” 

“It finally got to the point where I couldn’t ignore it. She would make comments about how I never had any time for her because of my family, and that my family was trying to keep us apart. I tried to end it, but she would just act like everything was fine and keep trying to see me. So I told my parents about her, thought they might be able to get the police involved, since what she was doing had crossed over into the realm of stalking a long time ago,” Stiles realized that his hands were clenched into fists at his sides, and his heart was racing. Derek’s family died in a fire. It didn’t take someone with Stiles’ IQ to figure out what happened next. 

“She… She _burned your house down_ because you broke up with her?” Stiles choked out, the horror etched plainly across his face. He thought he might be sick. 

“I still have no idea how she did it, but she waited for me to leave for work, and when I got home, it was just a pile of smoldering debris. My little sisters…” Derek tried to stifle a dry sob, but Stiles pushed their foreheads together and started murmuring every comforting thing he could think of into Derek’s ear. 

“Shh, it’s okay, Derek, look at me, c’mon. It wasn’t your fault, and there’s nothing you can do about it now-”

“But it _was my fault_ , Stiles!” Derek roared, startling Stiles enough that he fell backwards and almost hit his head on a table leg. 

“It was completely, and totally, my fucking fault. I couldn’t resist a nice piece of ass and it got my entire family murdered. And after she had destroyed my home and killed everyone I loved, do you know what she did next?” Derek’s voice had an almost frightening shrillness to it now, like just talking about all of this made him go slightly insane. Stiles couldn’t blame him, though. 

“She tracked me down, somehow. I had a little money, and I was staying in a motel until I could figure out somewhere more permanent to live,” he chuckled then, gesturing with his arms to indicate that the prison was that more permanent place. “She found me while I was filling up my ice bucket. She tried to tell me she was sorry. She said that she only did it so we could be together. When she tried to kiss me, I hit her in the back of the head with the ice bucket. I kept hitting her until she stopped moving,” Derek was scowling, his head turned away from Stiles. Stiles couldn’t tell if he was ashamed of what he had done to Kate or if the whole story just left a bad taste in his mouth. 

“Hey, if I could bludgeon cancer to death with an ice bucket, I would. I can’t believe anyone would blame you for that after what she did…” 

“She was never convicted for the fire, so to the jury it just looked like cut and dry murder. But I was just a kid who had lost his whole family, so they gave me the minimum sentence.” 

“Which is…?”

“For second degree murder in the state of California, it’s 15 years,” Derek said it with absolutely no emotion, like he had managed to shut down the part of him that felt sadness or pain. 

Stiles whistled slowly. “So how many do you have left?” 

“Six,” Derek said, and Stiles felt like the shittiest person ever for immediately calculating how old that made him, instead of focusing on how upset Derek was (he was 24). 

“That’s such unfair bullshit. You’re stuck in here for… for _avenging_ your family while rapists get, like, 6 months. It’s fucking ridiculous, I mean-” 

“Stiles, calm down,” Stiles realized he had been verging on shouting, and he felt his cheeks flush in embarrassment at the way Derek was looking at him. 

“I’ve made my peace with it. I realized it’s just smarter not to dwell on the shit I can’t change,” Derek finally seemed to be returning to his regular self, and Stiles felt comfortable enough to move a little bit closer to him without fear of being smacked. 

They sat next to each other in relatively comfortable silence for a few minutes before Stiles turned his head to look at Derek and noticed that he seemed to be trying to hide a grin. 

“What’re you smiling about?” Stiles teased, poking Derek in the arm. Derek didn’t turn his head, but his eyes swiveled to the side to look at Stiles. He smiled a little bit wider. 

“Just realizing… You’re the first person I’ve ever told that story to. The first person I’ve been able to trust enough since-” 

Stiles was moving forward before he even realized what he was doing, pressing his lips chastely but firmly against Derek’s unsuspecting ones. Derek grunted in surprise but it only took a few seconds for him to slide a hand to the back of Stiles’ head and pull him closer. 

Stiles was running on pure adrenaline and he was hoping that Derek wouldn’t notice his complete lack of kissing technique, but from the way Derek was moaning into his mouth he figured he was doing okay so far. Speaking of Derek moaning, shit, that was really hot. 

Stiles grabbed blindly at the fabric of Derek’s jumpsuit and tried to maneuver himself into Derek’s lap, but in the process he ended up pressing his very noticeable erection against Derek’s thigh, and that seemed to sober Derek up instantly because he jerked away from Stiles and stood up in one quick movement. 

“What are you doing?” Derek had the nerve to actually look affronted, even though he had been more than reciprocating only a few seconds ago. 

“What do you mean what am _I_ doing? Are you seriously gonna act like you weren’t just groping my ass-”

“You’re too young-”

“I hate you so much,” Stiles stood up too, and shoved Derek against the bookcase, causing a few books to fall to the floor around their feet. 

He appreciated that Derek was allowing himself to be held in place even though he could have shoved Stiles away easily. 

“You can play the noble gentleman card all you want, but if you think I haven’t noticed the way you look at me, you’re as dumb as you are pretty,” Stiles said, backing off from Derek a fraction of an inch and waiting to see how he would respond to being called out on his cradle robbing ways. 

Derek just blinked and then smiled again. Stiles could definitely get used to seeing that smile. 

“So you think I’m pretty?” Derek smirked, and Stiles almost choked on his own tongue when he realized Derek was repeating his own words from days ago back at him. 

This time it was Derek who surged forward and pressed their mouths together, but it was hungrier than before, more urgent, and soon Stiles found himself pinned down against the vaguely smelly library rug with a 24-year-old convicted killer grinding against him. 

Derek’s beard was kind of prickly but it felt strangely erotic when he dragged it slowly down the length of Stiles’ neck, and Stiles tried to control the stream of gasped out words ( _fuck! oh! Derek!_ ) that were pouring from his mouth, but he wasn’t having much luck. This was the first sexual encounter he had ever had, and he was dangerously close to coming just from making out on the ground. 

“Can we-?” Stiles didn’t know how to phrase the question _Can we jerk each other off_ without sounding like an idiot, so instead he just reached between their bodies and attempted to pull down the zipper of Derek’s jumpsuit. 

“I hate these things,” Stiles laughed awkwardly, and Derek gently pushed his hand away so he could unzip it himself. “Is this really happening?” Stiles asked out loud, before he could stop himself. Even just the small sliver of skin where Derek’s undershirt had been rucked up was enough to turn Stiles’ brain to mush, and he wasn’t really paying attention to what was coming out of his mouth. He was much more concerned with what he could be putting _in_ his mouth…

“ _Shit_ , Stiles,” Derek gasped as Stiles reached eagerly through the opening in his jumpsuit to wrap his hand around Derek’s cock. 

“Yeah,” Stiles mumbled, too distracted by the feel of someone else’s dick in his hand to say anything polysyllabic. He knew his hand was shaking as it stroked up and down Derek’s cock, but he couldn’t stop it. Derek was palming him through his own jumpsuit, and all of the sensations were getting to be too much, and he was terrified he would fuck up and Derek would just get up and leave. 

“Stiles, stop,” Derek whispered, and Stiles felt his stomach drop. Oh God, he was bad at handjobs, he knew it, he was the worst gay guy ever. Wait, no, he wasn’t gay, it was just Derek, and that wasn’t important because _why was Derek telling him to stop_?

“What? Why-” Stiles demanded at full volume, before Derek shoved a hand over his mouth and glared down at him. 

“There’s a guard in the hallway, I just saw a flashlight,” Stiles almost laughed in relief, before he realized how much trouble they would be in if they were caught. He just nodded at Derek and as soon and he was free from underneath him, he shuffled to his feet and hid behind the nearest bookshelf. Derek motioned wordlessly to Stiles to leave through the doors on the other side of the room. Stiles assumed Derek would be going the other way, but then it hit him he actually had no idea which cell block Derek was even in. 

Before he could ask, or even say a hushed goodbye, Derek was gone, and Stiles quickly got the hell out of there too. It was almost too easy to sneak back into his cell, and he was safely snuggled up with his itchy wool blanket by the time the guards came by to do bunk checks. 

It was about an hour after that Scott’s head appeared over the side of the bed, looking irritated but also adorably ruffled from sleep. 

“Why are you humming? Are you happy about something?” Stiles stopped humming immediately. He had barely realized he was doing it. He grinned up at Scott and sighed before folding his arms behind his head and closing his eyes. 

“Oh, it’s nothing, really. I’m just in love,” Stiles elected to keep the _with a murderer_ part to himself for the time being.


	6. Chapter 6

Stiles had learned to find amusement and joy in all the little things since arriving at California Correctional, and Guard Finstock’s movie quote recitations during breakfast were definitely at the top of that list. Finstock was everyone’s favorite prison employee, ranking above even the intimidatingly pretty blonde Erica who worked in the infirmary, because he was so lenient and basically let the inmates get away with whatever they wanted. 

Stiles was busy halfheartedly pushing some soggy french toast sticks around his tray and listening to Finstock’s rendition of Aragorn’s speech from Return of the King when he felt something hit the back of his head. He whipped around to try to find the culprit, but they had already been absorbed into the throng of prisoners entering the crowded cafeteria. Stiles reached down and retrieved the crumpled up napkin that was resting on the floor next to Isaac’s shoe, and discreetly unfolded it under the table. He almost choked on his orange juice when he saw the words there. 

_thinking about you. want to you see you again. -DH_

“Whatcha got there, Stilinski?” Jackson startled the grin right off of Stiles’ face, and somehow managed to snatch the illicit love note napkin out of his grasp. 

“Nothing! That’s totally not… anything…” Stiles sighed in defeat as Jackson held the note up to his face to decipher the tiny scrawl. He felt his cheeks turn bright pink as Scott and Danny leaned over to sneak a peek too. Stiles buried his head in his hands and groaned. 

“Not bad, looks like Stilinski’s bagged himself a top dog,” Jackson smirked as he tossed the napkin face up onto the center of the table, and Isaac and Boyd leaned in with poorly concealed interest. 

“What’s that supposed to mean?” Stiles snapped defensively, grabbing the napkin and shoving it into his pocket. 

“Just that you’re not as dumb as you look. Getting into Hale’s pants was a good move, as far as gaining protection goes. Judging by this note, you’ve already got him pretty whipped,” Stiles gaped at Jackson’s stupid smug face for at least 30 seconds before he was able to come up with a response to that. 

“Wait, lemme get this straight. You think I _seduced_ Derek so he would, what, grow attached to me and not let anybody mess with me? You think I’m that much of a manipulative asshole?” Finstock chose that particular moment to launch into the speech from Braveheart, and they were all distracted from their confrontation for a few seconds as they watched him shout about tyranny and freedom. 

When Jackson finally turned back around to face Stiles, he was _still_ smirking. Stupid assface. 

“I don’t really give a shit if you’re manipulating him or not, I was just trying to congratulate you on making a strategic choice of who to fuck,” Jackson shrugged and went back to stuffing his face with scrambled eggs, and Stiles was forced to turn and look right into Scott’s confused eyes. 

“So that’s why you kept asking about Derek? You like him? _Like_ like?” Scott looked only slightly alarmed by the idea, and Stiles was pretty sure he was just beating himself up for not realizing it sooner. 

“Uh, yeah, sort of. I don’t know what you guys are always talking about, either, he’s not that bad. He’s actually pretty nice once you get to know him.” 

“Yeah, I bet he’s _real_ nice, isn’t he, Stilinski?” Jackson laughed, and Stiles huffed a frustrated sigh before standing up to leave, but Jackson grabbed his sleeve and pulled him back down. 

“Hey, I was just kidding around. I think you and Derek would make an adorable couple,” Stiles wanted to punch Jackson, who was clearly still making fun of him, but before he could so much as shove at him angrily, Jackson was jumping up from the table and motioning for everyone to stay where they were. 

“Uh. What’s he doing?” Danny asked, and the rest of them just shrugged, watching as Jackson approached Guard Finstock and began talking to him. He was just out of earshot, but Stiles had a clear view of Finstock’s face, and was able to see as a range of emotions passed over his face, finally ending with him laughing hysterically. 

“You’ve gotta be kidding me!” Finstock’s booming voice was easy to hear as he shouted from across the room, but Jackson just kept at it, and after another minute or so he came swaggering back over to the table, looking pleased with himself. 

“That was easier than I thought it’d be,” Jackson said simply, taking a big gulp of his grape juice. 

“And what was “that” exactly?” Danny asked, clearly amused by the whole situation. 

“Oh,” Jackson said, like he had already forgotten what they were talking about, “I just got Finstock to agree to let me trade cells with Stiles, here.” 

“What? Why the fuck would you do that, I’m already cellmates with Scott!” 

Isaac was staring at Stiles like he was mentally deficient, and Boyd and Danny seemed to be in on the joke too. “What?” Stiles asked agitatedly. 

“Do you seriously not know?” Isaac asked, his expression softening slightly. 

“Know what? Jesus Christ, can somebody just fill me in already?” Stiles knew his voice was getting shrill, but he had no idea what was going on and it made him nervous that everyone else somehow seemed to. 

“Derek and Jackson are cellmates, man,” Scott said, looking anywhere but Stiles’ eyes. Stiles instantly started scanning his mental conversation logs for _any_ mention of this little fact, but he couldn’t remember a damn thing. 

“How… How the _fuck_ did that never come up in conversation when I was trying to find out information on him? I don’t even know what to say to you people...” Stiles trailed off, but then his mind was snapped back to the real issue at hand. 

“Wait. So you seriously got Finstock to switch us? Like, I can just go to Derek’s cell, where he sleeps, in his _bed_ , and I-” Stiles abruptly stopped talking when he noticed the expression on Scott’s face, like he was going to vomit, but it didn’t stop the excitement from growing inside him and threatening to burst out of him in manic laughter. 

“Jackson, I can’t believe I ever doubted you, you beautiful, beautiful douchebag!” Stiles laughed and pressed a closed mouth kiss to Jackson’s forehead. 

“Ew. Weird. Never do that again,” Jackson said, but he still smiled back at Stiles. “Just remember this the next time I need a favor, yeah?” Stiles nodded enthusiastically, and the rest of the guys rolled their eyes in his general direction. 

“How did you do it, though? I mean, I know Finstock’s a pushover, but still,” Boyd asked. 

“I just told him that Derek snored like a motherfucker and I couldn’t handle it anymore,” Jackson said.

“Yeah, but that can’t be all you told him,” Isaac said, while simultaneously sneaking a piece of bacon from Scott’s tray. 

“I may have also mentioned that Stilinski thought his impressions were shit, and it would be a nice way to get back at him to stick him in a cell with Derek’s atomic snoring,” Stiles raised his eyebrows; he was actually sort of impressed. 

“That’s kind of brilliant, dude,” Stiles said, and they all laughed as the bell went off signaling that breakfast was over. 

Stiles hoped the thing about Derek snoring wasn’t actually true, even though it wasn’t likely that they’d be doing much sleeping.

* * *  
As much as Stiles had wanted to rush immediately to his new living quarters, his daily work schedule had other plans for him. He was on laundry duty from noon until 5, and then he had to sweep the kitchen, and _then_ he had to organize books in the library because he had signed up to do that days ago. By the time lights out was about to be called, he barely had enough time to retrieve his few possessions from the cell he used to share with Scott, have a quick round of (totally manly and not lame) goodbye hugs, and then rush back to Cell Block A before the guards started bunk checks. 

It was weird being in this part of the prison. He didn’t recognize a single glowering face that he passed by while walking between the row of cells. There was definitely a different energy here, and Stiles wondered with a hint of apprehension if maybe he had managed to get himself relocated to the hardcore cell block. He wasn’t sure if they grouped people by the severity of their crimes, but Derek had killed someone and Jackson may or may not have beaten someone to death, so it was a real possibility. 

The guard who had been escorting him stopped in front of the last cell on the left, unlocked it, and jerked his head to motion for Stiles to move. Stiles stepped inside quickly, not realizing he was holding his breath until his lungs started to burn. He was man enough to admit he was nervous; sharing a room with the guy who both terrified him beyond measure and was the star of 100% of his jerk-off fantasies seemed like a reasonable thing to be nervous about. 

The guard slammed the cell door behind him and left, leaving Stiles to stare like a deer in headlights at Derek’s motionless form, relaxed across the bottom bunk, his face concealed behind a tattered copy of _The Count of Monte Cristo_. Derek was clearly a man who enjoyed his classic literature. 

“Uhhh,” Stiles said. Very smooth. 

“Jackson, did you talk to Stiles today? Did he say anything about-” Derek dropped the book to his chest to look up at who he obviously assumed to be Jackson. All of the color drained from his cheeks immediately when his eyes met Stiles’.

Stiles tried to ignore the fact that Derek was wearing _thick rimmed reading glasses_ and focus on the fact that he wasn’t reacting quite as Stiles had hoped he would. Derek had pushed himself up from his bed and was standing against the wall, his shoulders clearly tensed. Emboldened by the possibility that maybe Derek was just as nervous as he was, Stiles tossed his things onto the top bunk and took a few steps closer to Derek, attempting his very best bedroom eyes as he went. 

“Hey. So… Are we gonna fuck or what? Because I don’t have all day,” Stiles gave himself a mental pat on the back for managing to sound nonchalant and jokey but also obviously being kind of serious. He laughed at his own blinding wit, but Derek still had the same stoney expression plastered across his face. 

“Oh, um, I was just joking. I mean, no, I wasn’t, but I just thought-”

“You’re too young,” Derek spat out, crossing his arms in a defensive position and scowling at the floor. 

“Yeah, but, what about last night? You didn’t seem to have a problem with it when my hand was down your pants,” Stiles said, trying to hide the fact that he was starting to shake. Derek wasn’t making any sense, and now they were going to be stuck in this tiny room together indefinitely with no promise of fun sexual escapades. 

“That was a mistake. I’m sorry for taking advantage of you. Why are you even here?” Stiles opened his mouth to shout back a response, when he realized how stupid he would look if he told Derek the truth. He obviously had no interest in Stiles; he would probably laugh if he knew that Jackson had thought he was giving two lovebirds some alone time. 

“Jackson wanted to get away from your snoring,” he said, and without another word he pulled himself up into the top bunk and turned to face the wall. 

There was no way he could have misinterpreted Derek’s feelings for him so severely. There had been soul bearing conversations, and saving from prison yard thugs, and making out! Stiles had no choice but to come to the conclusion that Derek was too damaged to have real feelings and he had just been toying with Stiles, messing with the fresh meat for a bit of amusement. That still didn’t feel right, but he didn’t feel like thinking about it anymore. He shoved his head under his pillow and tried to fall asleep, trying his best not to listen to Derek’s even breathing three feet below him. 

* * * 

_Normally Derek would have hated being on janitor duty, but the demanding nature of the work was just what he needed to get his mind off of Stiles. It wasn’t exactly ideal that he was working with Lahey for the day, since he knew Stiles was friends with him, but he could deal with it._

_Lahey had been uncharacteristically quiet all day, but Derek wasn’t stupid enough to ask him if anything was wrong. He was just going to mop the hallway in silence, and think about everything except for the fact that Stiles was sitting back in his room, completely ready and willing to do whatever Derek wanted with him. Derek knew there were worse problems to have, but since he had decided not to be “that guy” who fucked sixteen year olds who didn’t know any better, it was a particularly tortuous dilemma. Not to mention that after the way he’d acted last night, Stiles probably wanted nothing to do with him anymore. Which was good. Really. That was what Derek had been going for with his noble little speech about what happened in the library being a mistake. Right?_

_“Hey Hale, can you pass me the Borax? There’s a vomit stain by the water fountain that does_ not _want to come off, and-” Isaac stopped talking when they both heard the distinct sound of something heavy falling to the floor. It sounded like it came from down the hall._

_“What was that?” Lahey asked, putting his mop down slowly in the bucket and inching toward the source of the commotion._

_“How should I know?” Derek snapped back at him, but he put his mop down too and followed Isaac cautiously down the hall. There were more sounds, faint enough not to be discernable but loud enough to be heard._

_“Sounds like it’s coming from the vents,” Derek whispered, pointing above their heads._

_“Yeah. Yeah I think you’re right. Any idea where the vents lead?”_

_“No. But we’re near the showers that have been closed for maintenance, that seems like a safe assumption.” Derek said, and they barely had time to share a look of “Why the fuck not?” before they were rushing down the hall, turning down the corridor when they got to the showers. Derek put a finger over his lips to signal for Lahey to be quiet, and he just rolled his eyes in response._

_They both pressed their ears to the wall, but without the vent, they could barely hear a thing._

_“We’ve got to get closer. I’m going in,” Lahey had pushed the door open before Derek could say anything to stop him, and since they were likely being paranoid about the level of danger anyway, Derek shrugged and followed him in. Once they were inside, the voices became not only distinguishable but almost at the level of shouting. Lahey’s jaw visibly dropped when it became clear who the speakers were, and Derek put a finger to his lips emphatically to tell him to stay quiet, but it was useless._

_“Gerard?” Lahey whisper-shouted back at Derek, as he inched around the cinderblock wall separating them from the noise. “And who is that? Greenberg? Sounds like Greenberg…” Derek was going to beat the hell out of Lahey for this if they got out unscathed. Lahey was continuing to move closer to the sounds of shouting and what was probably open-handed smacking, and Derek could do nothing but follow cautiously behind him._

_When they slowly poked their heads around the wall, they were met with the sight of three men, all facing away from them, one tied to an old rolling desk chair. They watched in silence as Gerard paced back and forth in front of the bloodied man, Greenberg, wringing his hands in what appeared to be frustration. Derek didn’t know the third man well, but he was pretty sure his name was Daehler, and that he had a penchant for snitching and dirty dealings. There seemed to be a lot of that going around lately._

_“Now, tell me, Greenberg,” Gerard all but spat in the immobile man’s face, “How is it exactly that you managed to lose_ an entire kilo of cocaine?” _Greenberg’s eyes never left the floor tiles, even as Gerard swung a punch at him out of nowhere. Gerard was panting with rage, and Derek felt his stomach turn sour at the look he saw in the old man’s eyes. He was capable of murder, and it was very possible they were about to bear witness to it if they didn’t get the fuck out there._

_“Isaac, we need to leave, come on,” Derek yanked on the sleeve of Lahey’s jumpsuit, but he wasn’t anticipating Isaac’s lack of resistance, and they ended up tripping over each other and landing right at Gerard’s feet._

_“Fuck, run!” Derek managed to pull Lahey to his feet but that was as far as they got. Matt was blocking the exit, wielding a crowbar and a manic grin._

_“Boss?” He looked to Argent, awaiting instruction. The older man also seemed to be taking some kind of perverse pleasure in the situation, and he smiled at Matt before holding out a hand._

_“Wait just a minute, son, I’d like for them to see something first,” he walked calmly back over to Greenberg, who was struggling against his restraints and screaming through the rag shoved in his mouth. Gerard moved to stand behind him, placing his hands on Greenberg’s shoulders._

_“Now, what have we learned about not following orders?” Gerard asked to seemingly no one in particular. Everyone was silent, and even Greenberg ceased his muffled yelling._

__“Don’t. Do. It.” _Gerard snarled out, before gripping Greenberg’s head on both sides and twisting until there was a sickening snap. Isaac gasped out loud, but Derek just continued glaring pointedly at the ceiling. He was terrified, but that didn’t mean he was going to show weakness in front of the crazy old bastard._

_Gerard brushed his hands off on the front of his trousers, before walking back over towards them. He nodded at Matt, who swiftly hit Lahey over the head with the crowbar. Derek tried to get the upper hand on Daehler while he was distracted with Isaac, but he was quick, and soon Derek’s skull was radiating with blinding pain, and everything went dark._

* * * 

Stiles was attempting to pay attention to the game of checkers he was currently playing with Scott in the recreation hall, but his mind kept drifting to other things. Specifically big, broody, hairy things who were totally sending mixed signals about wanting to fuck and causing Stiles a lot of emotional hardship. 

“Stilinski! Hello? It’s your move,” Jackson threw a plastic checker at Stiles’ ear, and he snapped out of his angry reverie. 

“Yeah, I know, just give me a goddamn minute. Also, why are you even here?” Stiles groused, reluctantly turning his attention back to the board. 

“What’s up his ass today?” Jackson turned to Scott, who was staring intently at the board, planning his next move. “Or should I be asking _who_ was up his ass last night?” Jackson sent one of his trademark smirks Stiles’ way, but Stiles just frowned and moved his black checker across the board, snatching up three of Scott’s red ones. Scott glared at him, but retaliated with a move of his own before registering the fact the Jackson was even speaking to him. 

“How about we try _not_ talking about my friend’s sex life,” Scott said with an exaggerated grimace. Stiles kept his expression as neutral as possible, hoping Jackson would just move on, but he had no such luck. 

“Really though, I’m dying to know what you two crazy kids got up to. This is as close to entertainment as I can get in here,” Jackson said. 

Part of Stiles was tempted to tell Jackson to go fuck himself, but another, apparently more dominant part of him wanted to get a second opinion on Derek’s weird behavior. 

“Fine. You wanna know? I got totally, _painfully_ rejected, and we haven’t spoken since. Satisfied?” Scott looked like he wanted to say something well-meaning but ultimately pitying and Stiles just could _not_ handle that right now, so he stood up and backed away from the chess board. 

“No, don’t start, okay? This is all just stupid and Derek is obviously crazy and I need to just forget about my stupid feelings and move on-”

“Are you really this much of a moron, Stilinski?” Jackson stood up too, and stepped towards Stiles so they were face to face. 

“Uh. What?” Stiles asked. 

“Hale’s obviously into you, you’re like, in love with him or whatever. Are you just gonna give up like this?” Jackson seemed to be genuinely worked up over all of this, and Stiles felt the ridiculous urge to start laughing. 

“Why do you care so much? It’s actually sort of weird, no offense,” Stiles scratched his head and tried not to look directly at Jackson’s face. This was possibly the strangest interaction he had ever had. 

“Because I know a little something about love, and I know that if you’ve got a chance at something real, you’d be a fucking idiot to just let it slip through your fingers-”

“You’re right!” Scott yelped as he shot out of his chair. Stiles and Jackson both whipped around to stare at him in confusion. “I have to tell Isaac how I feel!” Scott was grinning, and apparently it was contagious, because Stiles found himself laughing at the craziness that was his life. 

“Yeah, uh, me too. But, you know, with Derek…” Jackson arched an eyebrow at the two of them, before cracking a small smile as well. 

“People in love make me sick, you know,” Jackson said. Stiles just scoffed at him and put his arm around Scott, pulling him into a half hug. 

“Now we just have to find them both and confess our deeply embarrassing feelings. Should be a piece of cake, right?” Stiles said. “But I haven’t seen Derek since yesterday, do you either of you know where he might be?” 

When Boyd purposefully cleared his throat from the doorway behind them, they all jumped.

“I didn’t want to say anything…” He looked around the room before walking over to the corner where they were standing. He gestured for them to lean in towards him, and when he spoke again it was in a frantic whisper. Or at least as close to frantic as Boyd was capable of getting.

“I saw Derek and Isaac getting dragged into a storage closet in the guard’s chambers when I was returning the sandwich cart last night,” Stiles, Scott, and Jackson stared at Boyd for a solid minute before Stiles finally spoke. 

“Why… _Why the fuck would you not want to say anything about that?_ ” Boyd’s face remained devoid of expression as always, but he had the decency to look at the floor in shame. 

“I didn’t want to get mixed up in whatever it was. But I can show you where they are, if they haven’t been moved yet. Or, you know…” 

“Don’t say it! We get it, just take us there, _right_ now,” Scott said, in a voice more commanding and confident than Stiles had ever heard him use. Boyd nodded solemnly and took off at a jog through the doorway, and the rest of them followed. Stiles had the sickening feeling that he knew exactly who was behind this, and he just hoped that they weren’t too late to stop whatever the fuck Gerard Argent was planning.


	7. Chapter 7

Stiles could hear the sound of his heart hammering in his ears by the time the four of them came to an abrupt halt outside of an extremely nondescript, windowless door. His lungs were burning with the effort of running from one side of the prison to the other, but Jackson and Scott were gulping in breaths of air, too, so at least he didn’t have to feel ashamed of it. Boyd, as always, seemed completely nonplussed by the entire situation, even the looming reality that Derek and Isaac’s cooling corpses might be waiting for them on the other side of that door. 

Scott reached for the door handle, and no one was surprised when it stayed firmly locked in place as he attempted to turn it. 

“So what now?” Scott asked, before giving the door a solid kick for good measure. Stiles tried to calm his jumbled thoughts enough to think of an answer, but he had never been good at staying focused under pressure and his mind was a blur. He turned around to survey the rest of the empty hallway for _anything_ that might be able to help them get into that room. When his eyes skimmed over one of the door placards marked “Jessica Bartlet, Administrator,” he almost screamed, as something in his brain clicked into place. 

“I know what to do. Wait here,” Stiles said, before launching himself across the hallway and pushing his way through the door, which was mercifully unlocked. The small office was empty, but Stiles had assumed as much since it was past 6pm on a weekend. The desk took up most of the cramped space, and he had to practically contort his body to squeeze around behind it, but it was worth it when he opened the first drawer and found exactly what he was looking for. He reached into the small plastic tub and pulled out two paper clips before jumping over the desk and rushing back into the hall. 

“Are you gonna tell us what’s going on?” Scott asked, more agitated than Stiles had ever heard him. 

“Yeah, just, wait,” Stiles crouched down so the lock within the handle was at eye level. He hastily pulled the paper clips apart so they were in the shapes he needed, but when he tried to push the first piece of steel wire through the lock, he realized his hands were shaking too badly to do it. 

“ _Fuck_ ,” he sat back on his heels and wiped a hand across his face, trying to push back the tears that were starting to sting behind his eyelids. 

“Stiles, look at me,” Scott crouched down to his level, his gaze determined and oddly calming. He put both hands on Stiles’ shoulders and started taking exaggeratedly deep and slow breaths, indicating for Stiles to follow his lead. 

“You have to relax. Don’t think about anything that’s going on, it’s all going to be fine. Here,” Scott reached to pick the fallen paper clips up from the dirty tile floor where Stiles had dropped them, before folding them gently into his palm. “You can do this, buddy, just focus,” Stiles nodded, his attention returning to the task at hand. 

Lock picking was one of many basic skills that Stiles had picked up during his delinquent days, and under normal circumstances he would have been able to make quick work of a rudimentary handle lock like this one, but two of his friends’ lives were in the balance, and he felt like a thing like that was a pretty decent excuse for not being completely on top of his game. 

“Breathe, Stiles,” he whispered to himself, before inserting the first paperclip again. He jiggled it around a bit before adding the second one, and within seconds the door was clicking open and Scott was rushing through it, leaving Stiles to shake himself out of his reverie before jumping to his feet and heading in after him. 

It was nothing more than a slightly larger than average janitor’s closet, but it was the most beautiful room Stiles had ever seen, because in the center of it was Derek, fully alive and conscious. Isaac was there too, bound to Derek and the chairs they were sitting on with an excessive amount of rope. 

“Thank fuck, took you long enough,” Isaac exclaimed as Scott rushed to his side and started to untie the many knots keeping them in place. 

Stiles went to Derek, who was looking determinedly straight ahead at some bottles of bleach and mop buckets, but Stiles took his head in his hands and turned it to face him. 

“Are you okay? What the hell happened?” Derek huffed out a breath that sounded a lot like his resolve to ignore Stiles crumbling, and he finally looked up and made eye contact. 

“It was Gerard. We walked in on him and Matt Daehler right before they murdered Greenberg, and then to keep us from talking they brought us here. They could come back at any minute, we need to get out of here,” Stiles was nodding along as he clawed at the ropes, his nails too short to get a good grasp on the knots. Scott had already managed to free Isaac, so he shooed Stiles away and got to work untangling Derek too. 

Stiles couldn’t stop touching Derek, absent-mindedly running his hands over Derek’s arms and chest, making sure that he was really alive and solid and whole. He easily could have been killed too, probably would have been if they hadn’t gotten here before Gerard- 

“Guys, run!” Jackson came barreling through the doorway, followed by Boyd, who actually looked something other than bored for once. He looked terrified. 

“Gerard is coming, he just turned the corner, we have maybe 20 seconds at most-” Jackson was cut off by Gerard’s baton smashing against the side of his head, before catching Boyd on the underside of his jaw and sending him to the ground as well. 

“Fuck!” Stiles yelped, throwing his arms out defensively over Derek, who was finally free from the ropes, and pushing him, Scott, and Isaac as far back into the corner of the tiny room as possible. Gerard had a look of pure rage on his face, and he was advancing on them quickly, that fucking traitor Danny Mahealani close behind him. 

“I have not worked all these years to have you ruin it!” Gerard screamed, spittle flying from his mouth and landing on Stiles’ face. He squeezed his eyes shut, too afraid for his life to be disgusted. He was bracing for the impact, preparing to die as he heard the unmistakable sound of a bullet being chambered. 

He reached blindly for Derek’s hand, grasping it tightly and trying his hardest not to cry. When he heard a loud smashing sound and a body falling to the floor, he thought for sure that one of his friends was dead, but Derek was pulling on his hand, and through his haze of fear and adrenaline Stiles could make out his name being called. 

He opened his eyes slowly, inhaling sharply at the sight of Gerard’s body lying face down on the floor. Danny was standing over the old man, a fire extinguisher still raised in the air, and a small smirk on his face. 

“God, that guy was overdramatic,” Danny leaned down to check for a pulse on Jackson and then Boyd, before standing up and brushing his hands off on his pants. Stiles, Derek, Scott, and Isaac were all gaping at him, and his only response was to shrug and say, matter-of-factly, “Yeah, I’ve been working undercover with the FBI to stop drug trafficking in prisons all over the country.” 

“Ooookay,” Stiles said, his heart still hammering so fast he could barely breathe. They were actually safe. No one was going to die today. It was hard to process so many different emotions in such rapid succession, but since Danny was clearly busy with calling in back-up and Scott and Isaac had started making out on the other side of the room, he didn’t really have any other choice but to turn around and face Derek, who was already staring at him. 

“Hey,” Stiles said, his voice a little rough and shaky from the whole imminent death thing. 

“Hey,” Derek said back, chewing his bottom lip and refusing to make the situation any less awkward by saying something. The last time they had spoken had been less than pleasant, but Stiles felt like under the present circumstances they could forgo the social norms and just be happy that they’d survived. 

“I’m glad you’re not dead,” Stiles finally said, before sticking out his hand for the world’s most awkward handshake. Derek raised both eyebrows skeptically, but he still grasped Stiles’ hand and shook, holding on for slightly longer than necessary before letting their hands drop back to their sides. 

“You saved my life,” Derek said, the intensity behind his voice making Stiles’ knees feel like they were going to buckle. Stiles just laughed weakly, rubbing a hand over his buzzed hair and trying not to blush too furiously. 

“No dude, I picked a lock, Danny saved your life,” Derek actually smiled at that, and he reached towards Stiles to twine their fingers together. Stiles gulped, and he knew he was failing to hide the flush that was no surely covering his entire body. 

“I don’t actually care,” Derek said, tugging Stiles forward by his hand before pressing their mouths together softly, like he was asking for permission. Stiles made a small sound of surprise before reaching up and burying his hands in Derek’s hair, his tongue darting out to lick inside Derek’s mouth. 

“Ahem,” Danny’s voice shocked Stiles enough for him to jump away from Derek. He had completely forgotten there was anyone else in the room, let alone another set of dudes making out in tandem a few feet away. 

“Wow, uh, sorry about that…” Stiles said. Scott and Isaac were somehow still going at it, but instead of looking annoyed, Danny just laughed. 

“Don’t apologize, it’s not like it wasn’t fun to watch, but the wardens are on their way and you might not want them walking in on this gay love fest, hot as it may be,” Stiles nodded and smacked Scott on the back of the head, just seconds before a stampede of wardens, guards, police officers, and FBI agents came barreling into the room. 

Nobody was paying any attention to the four of them standing in their little corner, so Stiles leaned over and whispered in Derek’s ear, too quietly for even Scott or Isaac to hear. 

“To be continued?” He wiggled his eyebrows, and Derek looked at him incredulously. 

“Your dedication to making out with me is admirable, but I don’t think we’re going to have a minute to ourselves for a while. There are going to be interviews, hearings, a thorough investigation-” Stiles pressed a finger to Derek’s mouth, effectively shutting him up. 

“You and your excuses, man, do you want to have sex with me or don’t you?” Derek’s eyes bugged out of his head and he pulled Stiles’ hand away from his face. 

“I love how you’ve chosen to have this conversation about illegal underage sex in a room full of cops,” Derek grumbled, and Stiles just let out a full bodied laughed, because he could. He may still be incarcerated, but at least he wasn’t dead, and at least he had Derek and Scott and the rest of his motley crew of felon friends. Somehow he’d managed to feel happiness in one of the least likely places imaginable, and he _really_ didn’t want to think about what that said about him as a person. 

* * * 

“Stiles, stop,” Derek pressed a hand firmly against Stiles’ chest and rolled him so they were laying side by side in the tiny bunk. Stiles pouted dramatically and went back to stroking his hands along Derek’s muscled forearms. 

“You’re no fun.” 

“I’m just trying to keep you from doing something that you’ll regret-”

Stiles sat up at that, turning to glare at Derek, who was still lying on his back and looking up at the bunk above them. 

“No, you know what, I am so sick of this chivalry, dude. I know you have sappy mushy feelings about me and you can’t even try to pretend that you don’t,” Derek sighed and sat up too, turning so they were facing each other. 

“I’m not pretending anything, I just don’t want your first time to be on a prison cot with a man who’s 8 years older than you and doesn’t deserve you!” Derek ended up shouting by the end, and Stiles couldn’t handle how sad it made him that Derek was somehow deluded enough to think _he_ wasn’t good enough for _Stiles_ , as if it wasn’t the other way around. He decided to focus on anger instead of sadness, and he yelled right back at him. 

“Oh my God, I don’t give a shit about losing my virginity in a prison bunk! My life hasn’t exactly gone according to plan up to this point in case you hadn’t noticed, and I _want_ my first time to be with you! Asshole,” Stiles had somehow ended up back on top of Derek, and had his hands fisted in his white cotton undershirt. 

Derek’s expression softened, and he reached up to stroke his hand delicately over Stiles’ cheeks, before sighing again. 

“If this is _really_ what you want-” Stiles didn’t give him time to change his mind, he just started to nod enthusiastically, before going back to sucking sloppy kisses along Derek’s neck and undulating his body in an attempt to make Derek lose his resolve. If the deep moans that were coming from his throat were any indication, it was working. 

“Fine, fine, you win,” Derek panted, and Stiles has to restrain himself from pumping his fist in the air. “But you know I can’t _actually_ fuck you, right? Not without lube,” Derek sounded so breathless that Stiles was having a really hard time focusing on what he was saying, too turned on by the fact that he could make Derek fall apart like this. When he finally processed what he had said, Stiles just grinned, and pulled back so their faces were only a few inches apart. 

“Yeah, I know that. But I’m sure you can think of some other fun things to do to me,” Derek made a satisfying sound like he was choking on his own tongue, and Stiles smiled even wider. 

“Besides, the hearing is tomorrow, and the lawyers totally think we’re all gonna get released early for helping take down Argent’s drug empire or whatever. So we won’t have to wait too much longer to get to the good stuff, hopefully,” Derek just looked at him with his judgey face. 

“I’m concerned about your priorities if us having sex is more exciting to you than getting to go home,” Derek said, fondness evident in his voice. 

Stiles shrugged. He didn’t want to admit it out loud, not even to Derek, but he’d felt more at home here than he had in his house in Beacon Hills for a long time. Definitely since before his mom died. 

“Yeah, that’s cool too I guess. Now come on, let’s get this show on the road,” Stiles squirmed his way out of his white t-shirt and started to push his unzipped jumpsuit down his hips, but Derek stopped him by putting a hand over his. 

Stiles was prepared to go on another tirade about why he was completely and totally okay with this, but then instead of saying they should stop, Derek hooked his fingers in the orange fabric and said, softly, almost shyly, “Let me.” Stiles gasped, more out of shock than anything else, as Derek pulled his jumpsuit the rest of the way off, leaving Stiles in his plain white boxers and nothing else. 

“Your turn,” Stiles said, yanking Derek’s tank top off and throwing it on the floor with his own clothes. Derek looked too fucking good to be real spread out underneath him, his chest rising and falling rapidly and his pupils blown with lust. Stiles still felt uncomfortable with the idea that anyone would be attracted to him, but Derek was staring up at him like he wanted to devour him, and somehow that was more exciting than it was scary. 

“Okay, not gonna lie, might need you to take the lead here. I pretty much have _no_ idea what I’m doing and-” Derek seemed to snap out of whatever daze he’d been in, somehow managing to roll out from under Stiles and switch their positions without either of them falling off the cramped twin sized bed. The blatant display of strength made Stiles’ dick twitch in his underwear, and he made no attempt to hold back his helpless groan when Derek pinned his hands above his head.

“Stay just like this, can you do that?” Derek whispered against Stiles’ skin, mouthing along his bicep and tickling the sensitive areas with the brush of his lips. Stiles managed to get out a garbled “mmhmhhmm” sound before Derek started kissing a straight line down from Stiles’ clavicle towards his chest and stomach, eventually coming to the trail of light brown hair that disappeared into his boxers. 

“You done this before?” Stiles asked, trying not to be self conscious about the way his dick was tenting the front of his underwear very noticeably, right in front of Derek’s face. 

“Unfortunately, yes,” Derek said, and Stiles instantly regretted asking. He sometimes forgot how long Derek had been locked up in here, and he flashed back to the first conversation he had had with Isaac about how sexual favors were just a fact of life in prison. 

“Right. Sorry I asked, I really need to learn to shut the fuck up-” Derek chose that moment to lift up the waistband of his boxers and pull them off of him in one swift motion, causing his dick to spring up and almost hit Derek in the eye. 

Stiles was ready to be completely mortified and flee to his own bunk to try to forget this had ever happened, but instead of looking irritated at almost getting blinded by Stiles’ cock, Derek looked almost predatory, and the mischievous grin that followed did nothing to alter that perception. 

“Let’s see if this shuts you up,” Stiles whimpered pathetically at that, and when Derek wrapped his lips around the head of Stiles’ dick and _sucked_ , he couldn’t help but buck up into his mouth, trying to get more. 

Derek’s mouth was hot and wet and literally the greatest thing Stiles had ever felt, and he was clearly just getting started. The only word to describe Derek’s cock sucking technique was _enthusiastic_ , and he was alternating between teasing licks up the shaft and practically deep throating so quickly it was like he couldn’t decide which one he liked doing more. And the _sounds_ he was making, it was like he was the one getting his brain sucked out through his dick. 

“Derek, oh _Christ_ , you need to stop, I’m gonna, uh,” Stiles was trying to keep his hands above his head like Derek asked, but the urge to run his fingers through Derek’s hair and hold on for dear life was incredibly strong, and eventually he just gave in to the impulse and fisted both his hands in the soft hair at the nape of Derek’s neck. He knew he should try to pull Derek off him before he came after two minutes like the teenager that he was, but all he wanted to do was shove his head down further, fuck into his mouth for as long as he could. 

Derek made the decision for him, though, pulling off slowly and creating a string of spit from his swollen bottom lip to Stiles’ dick that was so obscene Stiles wanted to cry. 

“Sorry, I would never be able to live it down if I blew my load after like 2 seconds, and your mouth just felt _so good_ ,” Stiles gulped heavily as Derek leaned back on his heels and shimmied the rest of the way out of his jumpsuit and briefs, keeping his eyes locked with Stiles’ the whole time. 

Stiles knew his mouth was hanging open unattractively, but he was literally in bed with a man whose body was so perfect it would put Adonis to shame, and he was allowed to _touch_. He reached out slowly, carefully, and ran his fingers along the dips and curves of Derek’s abdominal muscles, which twitched under his fingers. He skimmed his nails along his chest, making Derek grunt when he brushed across a sensitive nipple. He wanted to get his hands on Derek’s cock, which was nothing short of magnificent, much like the rest of him, but Derek grabbed his wrist before he could. 

“This isn’t about me right now,” Derek said, although he didn’t sound very convincing, and his dick was jutting out from his body, hard and leaking precome, clearly at odds with his words. “Turn over, onto your stomach,” Stiles wanted to protest, but he also wanted to let Derek keep making him feel good, so he did as he was told. 

He felt uncomfortably exposed like this, laid out for Derek to see and probably a large portion of their cellblock to hear, but it was past 3 in the morning and hopefully most of them were asleep. Derek was busy positioning himself behind Stiles, kneeling with one leg on either side of Stiles’ body, and Stiles almost started hyperventilating when Derek shoved one of his threadbare pillows under Stiles’ hips and he realized what was about to happen to him. 

“Oh, God, Derek, do it, I’m ready,” Stiles could feel Derek’s hot breath ghosting over the back of his thighs, and he felt himself start to tremble with the anticipation of it. Derek started palming at his ass, spreading him open and exposing his hole but not going any further than that. Just when Stiles thought he would start sobbing if Derek didn’t touch him there soon, he felt Derek’s tongue, hot and persistent, licking along his rim, quick and teasing and so unlike any sensation Stiles had ever even _imagined_ that all he could do was push back into it and moan into the mattress. 

Derek’s tongue was like a jolt of electricity every time it swiped wetly across his skin, and when he started to push it every so slightly through the tight ring of muscle, Stiles thought his screams would attract the attention of every guard in the entire prison. 

“Shh, shh,” Derek’s voice was calming, not scolding, as he rubbed his hands comfortingly across Stiles’ back, which was now covered in a thin sheen of sweat. Stiles was gulping in air like a fish out of water, and it would probably wouldn’t take more than a slight breeze over his dick to make him come at this point. 

“You’re close?” Derek’s voice sounded strained, and Stiles couldn’t manage anything beyond nodding his head weakly. 

“Me too. Can I try one last thing?” Derek asked, and Stiles just nodded again, mumbling about how Derek could do whatever he wanted to him. 

Stiles was too far gone to move on his own, so he let Derek manhandle him into a kneeling position, with his legs pressed together. He actually had no idea what was happening now, but he realized with a jolt in his stomach just how implicitly he trusted Derek. 

When he felt Derek’s cock pressing between his thighs, just below his balls, he shuddered, and as soon as Derek reached around and wrapped a hand firmly around Stiles' dick, he felt his body start to spasm as he started to come. Derek was fucking between his thighs in earnest, grunting and sighing as he worked Stiles through his orgasm, and it was only a few more seconds before Derek was coming too, biting into the meat of Stiles’ shoulder to stop himself from making too much noise. 

Stiles’ arms gave out when his dick stopped pulsing onto the sheets, and he groaned unhappily as he landed in a wet spot of his own making. Derek fell down next to him, a look of tired happiness on his face, and Stiles felt an indescribable warmth spread through his entire body. 

“ _Wow_ , you have been holding out on me. I can’t even imagine how real sex could be better than that,” Stiles laughed and tried to squirm away when Derek grabbed him and pressed a kiss to the top of his head, and they ended up drifting off to sleep twisted up in each other’s arms. If some guards found them in the morning, the worst that would happen would be a verbal lashing and some public humiliation, but that seemed worth it to sleep next to each other for one night and be able to pretend they were just a normal, happy couple. 

* * * 

“Boyd, Vernon. Hale, Derek. Lahey, Isaac. McCall, Scott. Stilinski, Przemysław. Whittemore, Jackson. Please rise,” Judge Harris looked disdainfully down at them from his position behind the bench, and Stiles felt the bile rise in his stomach. His lawyer had seemed concerned that they’d gotten Harris assigned to their case, and the way he was looking at them now, like they were bugs that he’d love to squish, did not ease Stiles’ mind one bit. 

The courtroom they were in was small and dingy, but at least they’d been provided with real clothes to wear to the hearing, so Stiles felt a little bit less like the criminal scum Judge Harris was making him feel like. 

“You’re here today because you were all instrumental in the takedown of Gerard Argent, former head warden of the California Correctional Institution and the mastermind behind more than 30 different drug smuggling rings on the West coast. Is this correct?” Stiles wished he could reach for Derek’s hand right now for comfort, but they had Scott and Isaac standing between them, and he wouldn’t have dared hold another man’s hand in the middle of a courtroom to begin with. 

Not to mention the fact that he had seen his father slip through the doors a few minutes after the proceedings had gotten underway, and he wasn’t quite ready for him to know he liked men, which seemed a little ridiculous in retrospect, but still. 

“That’s correct, your honor. My clients are requesting immediate release, based upon not only their assistance in bringing Gerard Argent to justice, but their impeccable good behavior as well,” Kira Yukimura may have been a public defender just out of law school, but she was sharp as a tack, and Stiles trusted that she could get them what they wanted. 

Harris started to shuffle some papers around, and he took his sweet time peering down through his spectacles at file after file, until it got to the point where Stiles’ legs started to hurt from standing for so long. Finally, he pushed the papers aside and banged his gavel 3 times, and Stiles crossed his fingers behind his back, even though he knew it was childish. 

“For their service to the state of California, the prisoners will each have 4 years subtracted from their sentences. Case dismissed,” The room erupted in the overjoyed sounds of his friends celebration, and he let himself be pulled into a tight hug by Scott, who was grinning from ear to ear. Jackson slapped him on the back, and he looked over to see his father wiping a tear away from his eye. 

Derek even had a small smile for him as well when their eyes met, but Stiles couldn’t manage it. 4 years subtracted from their sentences. It meant that he, Scott, Isaac, Jackson, and Boyd would all be released immediately, but Derek, who still had 6 years remaining on his sentence, would not. 

Derek pulled him through the throng of friends and family who had rushed out to congratulate their loved ones. He cupped Stiles’ face in his hands, and smiled genuinely at him, wiping a tear away from Stiles’ cheek. 

“Hey, no, don’t cry. This is the best thing that could have happened,” Stiles wanted to hit him for saying that. They wouldn’t be able to see each other for 2 years, aside from visits through bulletproof glass. How could Derek think this was a good thing?

“What do you mean?” Stiles sniffled, hoping his dad would have the good sense to give them some space for a few minutes more.

“You can have a chance to be a regular teenager, finish high school… date other people. When I get out you’ll be 18, and we can be together for real. Stiles, look at me,” Stiles had been attempting to hold back tears by looking at his shoes, but Derek tilted his chin up and forced him to stare right into his eyes. 

“I want you to have a life. That’s what I want most in the world, do you understand me? So I better get a fucking letter in the mail telling me which Ivy League you get accepted to, got it?” Stiles felt the corner of his mouth lifting in an involuntary smile, and he nodded, even though they both knew full well an ex-con could never get accepted to an Ivy League school. He wrapped his arms around Derek and buried his face in the crook of his neck, breathing in the smell that was uniquely Derek that he wouldn’t be smelling again for a long time. 

“Son…” Stiles pulled away from Derek and spun around the face his father. The first thing he noticed was how un-rumpled his clothes were, and the bags that were absent from his eyes. He looked healthy, and steady on his feet like he hadn’t been drinking in the past few hours. 

“Dad?” Stiles’ voice felt so small, the hope blossoming in his chest that he might get to have his old dad back on top of everything else. His father just nodded before letting out a happy sob and pulling Stiles into his third hug of the day. 

“I missed you so much,” he whispered, knowing that his dad would understand the deeper meaning behind his words. He pulled away and saw the way his dad was eyeing up Derek with that distinctly protective look he used to get on his face whenever he would catch Stiles getting bullied by the other kids when he picked him up from school. 

“If you did anything to my son that he didn’t want-” Stiles had to grab his dad’s arm where it was pointing accusingly at Derek and place it back down by his side. 

“Dad, it wasn’t like that. Derek’s kind of… my boyfriend? But we’re waiting until I’m 18 to be together because he won’t get out of jail until then! That… sounded better in my head,” Stiles waited to see if his father would try to shoot Derek or strangle him with his own shoelaces, but instead he just reached out to shake Derek’s hand, who shook back hesitantly. 

“I don’t know what happened to my son while he was in here, but I can already tell that he’s changed for the better, and I’m grateful for that. Thank you,” he coughed out under his breath at the end, but Derek just smiled and nodded. 

“Son, we have to go, there’s some paperwork you need to fill out before they’ll release you,” Stiles looked back at Derek, who was also being ushered away by a bailiff, and Stiles did the only thing he could think to do. He threw out his arms dramatically and shouted, “I’ll wait for you!” and watched as Derek broke down in a fit of laughter from across the courtroom. 

Scott had appeared by his side with a beautiful middle aged woman who was wearing a pair of salmon colored scrubs. His dad introduced himself immediately and all but fell over himself telling her that they should let the boys talk to each other alone for a few minutes, and Stiles and Scott exchanged significant looks. 

_Brothers?_ Scott mouthed at him, and Stiles laughed. “Most definitely,” they both smiled at each other for a few more moments, because it was just that kind of day, before Scott said, more solemnly, “So that sucks about Derek, man. I’m really sorry,” Stiles sighed and nodded, but he found that he didn’t feel sad at all. Two years wasn’t all that long, was it? He’d already spent sixteen years without knowing Derek, he could handle two with the knowledge that he was here waiting for him, and they’d get to have fantastic “glad you’re out of prison” sex when he was released. 

Stiles groaned miserably at that thought, and Scott lifted an eyebrow at him. 

“Dude, I’m not gonna have sex again for two years. Fuck my life.” 

* * * 

Derek gets out in 1 year, 7 months for good behavior, and for starting a book club for the inmates. For their first date, Stiles takes him apartment hunting, and then they go for Thai food. Derek fucks him for the first time on the mattress on the floor of his new apartment. Stiles first says “I love you” when they’re on the sixth hole at Magical Mini Golf with Scott, Isaac, Jackson, and Boyd, and Derek says it 3 days later. 

Neither of them ever get so much as a parking ticket ever again. 

**Author's Note:**

> I have a Tumblr! Come say hey [@wolfymates](http://wolfymates.tumblr.com)


End file.
